Chloroacetyl chloride → HCID 21502944, compound

HRID 1288591Notes

Reaction equation

HRID 1288591 reaction equation
C(N(CC)CC)C.[C:8]1([S:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[NH:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:22][CH2:23][C:24](Cl)=[O:25]>C(Cl)Cl>[Cl:22][CH2:23][C:24]([N:15]=[S:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:25]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 608422S,S-Diphenylsulfilimine

Product 1

HCID 21502944HCID 21502944, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

A solution of 19.2 g (0.19 mol) of triethylamine in 50 ml of methylene chloride is added dropwise at room temperature, whilst stirring to a solution of 19 g (0.095 mol) of S,S-diphenylsulphilimine [compare Furukawa et al., Univ. Osaka: Tetrahedron Letters 1972, 1619-1622; Tamura et al., Univ. Osaka: Tetrahedron Letters 1972, 4137-4140] in 120 ml of methylene chloride and subsequently, whilst cooling slightly, a solution of 12.3 g (0.11 mol) of chloroacetyl chloride in 80 ml of methylene chloride is added dropwise. The mixture is stirred overnight at room temperature, the solvent is stripped off in vacuo, the residue is taken up in methylene chloride and the organic phase is washed with water until neutral. The product is then dried over sodium sulphate and the solution is evaporated in vacuo. N-(Chloroacetyl)-S,S-diphenylsulphilimine is obtained as an oily residue and is further processed as the crude product.

Workup

  1. temperaturesubsequently, whilst cooling slightly
  2. washthe organic phase is washed with water until neutral
  3. dry with materialThe product is then dried over sodium sulphate
  4. customthe solution is evaporated in vacuo

Sources & evidence

ORD record
ord-78fe221964094a779fa00b58a3ac09d0
Source dataset
uspto-grants-1976_10
Patent number
US03988467

Reaction notes

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