Acetic Acid → HCID 178509072, compound

HRID 1769813Notes

Reaction equation

HRID 1769813 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([S:7](Cl)(=[O:9])=[O:8])[N:3]=1.C(O)(=O)C.[F:15][C:16]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:17]=1[NH2:18]>>[NH2:1][C:2]1[NH:6][N:5]=[C:4]([S:7]([NH:18][C:17]2[C:16]([F:15])=[CH:22][CH:21]=[CH:20][C:19]=2[F:23])(=[O:9])=[O:8])[N:3]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 796472,6-DifluoroanilineHCID 178509069HCID 178509069, compound

Product 1

HCID 178509072HCID 178509072, compound

Procedure

5-Amino-3-chlorosulfonyl-1,2,4-triazole (20 g of about 92 percent purity, 0.1 mole) was slurried in 168 g (2.8 moles) of acetic acid and 14.2 g (0.11 moles) of 2,6-difluoroaniline were added. The mixture was stirred and heated at 90° C. for 11 hours at which time analysis by HPLC a 76 percent conversion to the title compound and 9 percent conversion to its 5-acetylamino derivative. Water was added and the mixture cooled to 10° C. The solids were collected by filtration, washed with water, and dried at 60° C. to obtain 14.8 g (53 percent of theory) of the title compound as a 96 percent purity product. Analysis of the filtrate by HPLC showed that it contained another 26 percent of theory and the total yield was 79 percent of theory.

Sources & evidence

ORD record
ord-d96f5b7be2e84fbb9bd4083149b60477
Source dataset
uspto-grants-1995_01
Patent number
US05382674

Reaction notes

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