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

HRID 1840647Notes

Reaction equation

HRID 1840647 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>>[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]([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 2

HCID 1165292,6-Dichloro-3-methylanilineYield 99.4%HCID 178425411HCID 178425411, compoundYield 95.3%

Procedure

4.4 g (0.025 mol) of 2,6-dichloro-3-methylaniline are heated to 110° C., 1.8 g (0.01 mol) of 5-amino-3-chlorosulfonyl-1,2,4-triazole are added under argon and the suspension is stirred for 90 minutes at this temperature. After work-up similar to example 1, 3.1 g (99.4% purity) of 2,6-dichloro-3-methylaniline and 1.81 g (95.3% 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 56.2%, and based on unrecovered aniline the yield is 76.1% of the theory.

Sources & evidence

ORD record
ord-dab519d1bc6b451b9c73a83553bb41fc
Source dataset
uspto-grants-2004_01
Patent number
US06680388B2

Reaction notes

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