Chlorosuccinimide → Ethyl 2-chloro-2-(methylsulfanyl)acetate

HRID 2423527Notes

Reaction equation

HRID 2423527 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][S:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(Cl)(Cl)(Cl)Cl>[Cl:1][CH:11]([S:10][CH3:9])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 78199Ethyl (methylthio)acetate

Product 1

HCID 10877535Ethyl 2-chloro-2-(methylsulfanyl)acetateYield 43%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Chlorosuccinimide (5.97 g, 44.71 mmol) was added portionwise to ethyl (methylthio)acetate (6.00 g, 44.71 mmol) in carbon tetrachloride (30 mL) at 0° C. under argon and the reaction was allowed to warm to room temperature and stirred for 17 hours. The reaction mixture was filtered and the filtrate was concentrated under vacuum. The oil was purified by distillation to give 3.22 g (43%) of ethyl chloro(methylthio)acetate as an oil. 1H NMR (400 MHz, d6-DMSO): δ 6.10 (s, 1H), 4.20 (q, J=7 Hz, 2H), 2.24 (s, 3H), 1.22 (t, J=7 Hz, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under vacuum
  3. distillationThe oil was purified by distillation

Sources & evidence

ORD record
ord-707d127d651840579f62a26bff842cf9
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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