Water → 2-chloro-N-(4-chlorobutyl-sulphonyl)-4-methyl-aniline

HRID 551221Notes

Reaction equation

HRID 551221 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[Cl:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15](Cl)(=[O:17])=[O:16].O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[NH:4][S:15]([CH2:14][CH2:13][CH2:12][CH2:11][Cl:10])(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 120072-Chloro-p-toluidineHCID 742124-Chlorobutane-1-sulphonyl chloride

Product 1

HCID 670486822-chloro-N-(4-chlorobutyl-sulphonyl)-4-methyl-aniline

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.30 ml (10.7 mmol) 2-chloro-4-methyl-aniline are placed in 30 ml of pyridine, combined with 2.67 g (10.5 mmol) 75% m 4-chlorobutyl-sulphonic acid chloride and stirred for 16 hours at ambient temperature. The reaction mixture is poured into water and extracted with ethyl acetate. The combined organic phases are washed with 6-molar hydrochloric acid, dried over sodium sulphate and evaporated down i. vac. The residue is purified by chromatography on silica gel (eluting gradient: petroleum ether/ethyl acetate=9:1→7:3).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases are washed with 6-molar hydrochloric acid
  3. dry with materialdried over sodium sulphate
  4. customevaporated down i
  5. customThe residue is purified by chromatography on silica gel (eluting gradient: petroleum ether/ethyl acetate=9:1→7:3)

Sources & evidence

ORD record
ord-4d703f5426c44af6b1c1cde516e6e502
Source dataset
uspto-grants-2011_05
Patent number
US07947700B2

Reaction notes

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