Benzenamine, 2-chloro-4-(methylsulfonyl)- → Acetanilide

Reaction equation

Cl[C:2]1[CH:8]=[C:7](S(C)(=O)=O)[CH:6]=[CH:5][C:3]=1[NH2:4].[C:13]([O-])(=[O:15])[CH3:14].[NH4+]>>[C:13]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:2]=1)(=[O:15])[CH3:14]

Participants

Reactant 2

HCID 25801Benzenamine, 2-chloro-4-(methylsulfonyl)-

HCID 517165Ammonium Acetate

Product 1

HCID 904Acetanilide

Procedure

2-Chloro-4-methylsulfonylaniline (2.06 g.) is diazotized and coupled with 3-(N-cyclohexyl-N-ethylamino)acetanilide (2.60 g.) in 40 ml. of 1:5 acid as described in Example 9, except that the coupling is buffered by the addition of ammonium acetate after the diazonium solution is added to the coupler. This azo compound, 2-(2-chloro-4-methylsulfonylphenylazo)-5-N-cyclohexyl-N-ethylamino)acetanilide, produces bright scarlet shades on polyester fibers.

Workup

additionis added to the coupler

Sources & evidence

ORD record: ord-55dd1a7aab3341e0b47257c2e81d03f9
Source dataset: uspto-grants-1979_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04140683

Reaction notes

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