Chloroacetyl chloride → HCID 54286174, compound

HRID 370097Notes

Reaction equation

HRID 370097 reaction equation
[NH2:1][C:2](=[N:6][OH:7])[CH2:3][S:4][CH3:5].[Cl:8][CH2:9][C:10](Cl)=[O:11].C(N(CC)CC)C>C(Cl)(Cl)Cl>[NH2:1][C:2](=[N:6][O:7][C:10]([CH2:9][Cl:8])=[O:11])[CH2:3][S:4][CH3:5]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 4126916HCID 4126916, compound

Product 1

HCID 54286174HCID 54286174, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

1-Amino-1-hydroxyimino-2-methylthioethane (11.32 g, 94.2 mmol) was suspended in dry chloroform (60 mL) under nitrogen. A solution of chloroacetyl chloride (7.5 mL, 94.2 mmol) in chloroform (20 mL) was added dropwise. After stirring for 1 hour, a solution of triethylamine (15.8 mL, 113 mmol) in chloroform (20 mL) was added dropwise. The reaction mixture was stirred for 15 minutes, then washed with water (2×70 mL), dried over sodium sulfate, concentrated in vacuo, and dried under vacuum to yield 11.4 g (62% yield) of 1-amino-1-((chloromethyl)carbonyloxy)imino-2-methylthioethane, as a brown semi-solid.

Workup

  1. stirringThe reaction mixture was stirred for 15 minutes
  2. washwashed with water (2×70 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customdried under vacuum

Sources & evidence

ORD record
ord-0a680751f58b43e6bc1b30d985abb531
Source dataset
uspto-grants-2000_10
Patent number
US06140351

Reaction notes

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