2,6-Dichloro-3-methylaniline → 2,6-Dichloro-3-methylaniline

HRID 1840649Notes

Reaction equation

HRID 1840649 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([S:7](Cl)(=[O:9])=[O:8])[N:3]=1.[Cl:11][C:12]1[C:18]([CH3:19])=[CH:17][CH:16]=[C:15]([Cl:20])[C:13]=1[NH2:14]>>[Cl:11][C:12]1[C:18]([CH3:19])=[CH:17][CH:16]=[C:15]([Cl:20])[C:13]=1[NH2:14].[NH2:1][C:2]1[NH:6][N:5]=[C:4]([S:7]([NH:14][C:13]2[C:15]([Cl:20])=[CH:16][CH:17]=[C:18]([CH3:19])[C:12]=2[Cl:11])(=[O:9])=[O:8])[N:3]=1

Participants

4

Reactant 2

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

Product 2

HCID 1165292,6-Dichloro-3-methylanilineYield 99%HCID 178425411HCID 178425411, compoundYield 90.8%

Conditions

Temperature
120 °C

Procedure

9.1 g (0.05 mol) of 5-amino-3-chlorosulfonyl-1,2,4-triazole (83.7% purity) are added in portions under argon over 1 hour to a melt of 22 g (0.125 mol) of 2,6-dichloro-3-methylaniline heated to 120° C. and stirred, and the suspension is stirred for 90 minutes at this temperature. After a similar work-up to example 1, 14.8 g (99.0% purity) of 2,6-dichloro-3-methylaniline and 13.5 g (90.8% purity) of 5-amino-N-(2,6-dichloro-3-methylphenyl)-1,2,4-triazole-3-sulfonamide are obtained. The theoretical yield is found to be 90.9%, and based on unrecovered aniline the yield is 98.1% of theory.

Workup

  1. stirringthe suspension is stirred for 90 minutes at this temperature

Sources & evidence

ORD record
ord-c2a21fbff492414cb266a608c328c7a6
Source dataset
uspto-grants-2004_01
Patent number
US06680388B2

Reaction notes

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