2,6-Dichloro-3-methylaniline → HCID 178425411, compound

HRID 1708579Notes

Reaction equation

HRID 1708579 reaction equation
[Cl:1][C:2]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([Cl:10])[C:3]=1[NH2:4].[NH2:11][C:12]1[NH:16][N:15]=[C:14]([S:17](Cl)(=[O:19])=[O:18])[N:13]=1>C(#N)C>[NH2:11][C:12]1[NH:16][N:15]=[C:14]([S:17]([NH:4][C:3]2[C:5]([Cl:10])=[CH:6][CH:7]=[C:8]([CH3:9])[C:2]=2[Cl:1])(=[O:19])=[O:18])[N:13]=1

Participants

4

Reactant 2

HCID 1165292,6-Dichloro-3-methylanilineHCID 178509069HCID 178509069, compound

Product 1

HCID 178425411HCID 178425411, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

In a manner similar to that described in Example 3, 8.8 g (0.05 mole) of 2,6-dichloro-3-methylaniline, 9.6 g (0.05 mole) of 5-amino-3-chlorosulfonyl-1,2,4-triazole and 25 ml of dry acetonitrile were stirred at about 65° C. for a total of 5 days. The reaction product was recovered as in Example 3 to obtain 10.8 g of the title compound as white solid, m.p. 240°-241° C. (dee.). This assayed by HPLC to be about 98 percent pure. The methylene chloride washes were concentrated to obtain 2.7 g of solid which was over 80 percent purity unreacted 2,6-dichloro-3-methylaniline. The yield of the desired sulfonamide was therefore 88 percent based on unrecovered aniline.

Workup

  1. customThe reaction product was recovered as in Example 3

Sources & evidence

ORD record
ord-e526ff31156e4e03b7351e4973ccda0a
Source dataset
uspto-grants-1994_10
Patent number
US05359079

Reaction notes

Loading…