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molecular formula C4H8Cl4NOP B028206 Bis(2-chloroethyl)phosphoramidic dichloride CAS No. 127-88-8

Bis(2-chloroethyl)phosphoramidic dichloride

Cat. No. B028206
M. Wt: 258.9 g/mol
InChI Key: IQPMYTNILJQKBS-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US07872134B2

Procedure details

Bis(2-chloroethyl)amine hydrochloride (6.3 g, 35 mmol), suspended in 80 mL dichloromethane, was cooled to −78° C. under argon and stirred. A solution of phosphoryl chloride (5.41 g, 35 mmol) in 10 mL dichloromethane, followed by a solution of triethylamine (3.53 g, 70 mmol) in 10 mL dichloromethane, was added slowly by syringe. Stirring was continued while the reaction mixture was allowed to warm to room temperature overnight. The reaction mixture was washed with 0.01N hydrochloric acid (3×25 mL), dried over magnesium sulfate, and concentrated under reduced pressure to give N,N-bis(2-chloroethyl)phosphoramidic dichloride as a light orange oil that solidified on standing (7.9 g, 87% yield). A 2.2 g aliquot of the crude N,N-bis(2-chloroethyl)phosphoramidic dichloride was purified by flash chromatography on a 12 g silica cartridge, eluting with a gradient of 100% hexane to 67% hexane/33% ethyl acetate over 10 minutes followed by 67% hexane/33% ethyl acetate for a further 10 minutes, to give 1.5 g pure N,N-bis(2-chloroethyl)phosphoramidic dichloride as a white solid after evaporation of the solvents. MS (ES): m/z=275 [C4H8Cl4NOP+NH4+].
Quantity
6.3 g
Type
reactant
Reaction Step One
Quantity
5.41 g
Type
reactant
Reaction Step Two
Quantity
3.53 g
Type
reactant
Reaction Step Three
Quantity
80 mL
Type
solvent
Reaction Step Four
Quantity
10 mL
Type
solvent
Reaction Step Five
Quantity
10 mL
Type
solvent
Reaction Step Six

Identifiers

REACTION_CXSMILES
Cl.[Cl:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][Cl:8].[P:9](Cl)([Cl:12])([Cl:11])=[O:10].C(N(CC)CC)C>ClCCl>[Cl:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][Cl:8])[P:9]([Cl:12])([Cl:11])=[O:10] |f:0.1|

Inputs

Step One
Name
Quantity
6.3 g
Type
reactant
Smiles
Cl.ClCCNCCCl
Step Two
Name
Quantity
5.41 g
Type
reactant
Smiles
P(=O)(Cl)(Cl)Cl
Step Three
Name
Quantity
3.53 g
Type
reactant
Smiles
C(C)N(CC)CC
Step Four
Name
Quantity
80 mL
Type
solvent
Smiles
ClCCl
Step Five
Name
Quantity
10 mL
Type
solvent
Smiles
ClCCl
Step Six
Name
Quantity
10 mL
Type
solvent
Smiles
ClCCl

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
-78 °C
Stirring
Type
CUSTOM
Details
stirred
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
was added slowly by syringe
STIRRING
Type
STIRRING
Details
Stirring
TEMPERATURE
Type
TEMPERATURE
Details
to warm to room temperature overnight
Duration
8 (± 8) h
WASH
Type
WASH
Details
The reaction mixture was washed with 0.01N hydrochloric acid (3×25 mL)
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
dried over magnesium sulfate
CONCENTRATION
Type
CONCENTRATION
Details
concentrated under reduced pressure

Outcomes

Product
Name
Type
product
Smiles
ClCCN(P(=O)(Cl)Cl)CCCl
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 87%

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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