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molecular formula C4H2N2S B073293 4-Cyanothiazole CAS No. 1452-15-9

4-Cyanothiazole

Cat. No. B073293
M. Wt: 110.14 g/mol
InChI Key: PNAFRZGWUVQUKH-UHFFFAOYSA-N
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Patent
US05310924

Procedure details

The product, thiabendazole, precipitated as it was formed in the reaction mixture. The reaction was monitored by gas chromatography and determined to be complete when the peaks corresponding to o-phenylenediamine and 4-cyanothiazole were negligible. The reaction mass was allowed to cool to 50° C. and 150 ml of 50° C. deionized water was added to thin the mixture before being vacuum filtered using a medium fritted glass filter. The solid product was washed four times with 300 ml portions of deionized water. The washed precipitate was dried overnight in a vacuum oven under 15-20" Hg and at a temperature of 80°-90° C. A total of 89.77 grams of thiabendazole were obtained which corresponds to an 89.3% yield. The color of dry thiabendazole was cream. High Performance Liquid Chromatography (HPLC) using a Hewlett-Packard Model 1090M showed that the purity was 98.77% (based on % area).
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Three
Yield
89.3%

Identifiers

REACTION_CXSMILES
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9]([C:11]1[N:12]=[CH:13][S:14][CH:15]=1)#N>O>[CH:4]1[CH:5]=[CH:6][C:1]2[N:8]=[C:9]([C:11]3[N:12]=[CH:13][S:14][CH:15]=3)[NH:7][C:2]=2[CH:3]=1

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C1(=C(C=CC=C1)N)N
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(#N)C=1N=CSC1
Step Three
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
50 °C
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
The product, thiabendazole, precipitated as it
CUSTOM
Type
CUSTOM
Details
was formed in the reaction mixture
CUSTOM
Type
CUSTOM
Details
150 ml of 50° C.
ADDITION
Type
ADDITION
Details
was added
FILTRATION
Type
FILTRATION
Details
filtered
FILTRATION
Type
FILTRATION
Details
filter
WASH
Type
WASH
Details
The solid product was washed four times with 300 ml portions of deionized water
CUSTOM
Type
CUSTOM
Details
The washed precipitate was dried overnight in a vacuum oven under 15-20" Hg and at a temperature of 80°-90° C
Duration
8 (± 8) h

Outcomes

Product
Name
Type
product
Smiles
C=1C=CC2=C(C1)NC(=N2)C3=CSC=N3
Measurements
Type Value Analysis
AMOUNT: MASS 89.77 g
YIELD: PERCENTYIELD 89.3%

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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