Methyl 2-chloroacrylate → 5-Chloro-5-methoxycarbonyl-3-thiapentanamide

HRID 465682

Reaction equation

HRID 465682 reaction equation
[SH:1][CH2:2][C:3]([NH2:5])=[O:4].O1CCOCC1.[Cl:12][C:13](=[CH2:18])[C:14]([O:16][CH3:17])=[O:15]>N1C=CC=CC=1>[Cl:12][CH:13]([C:14]([O:16][CH3:17])=[O:15])[CH2:18][S:1][CH2:2][C:3]([NH2:5])=[O:4]

Participants

5

Reactant 3

HCID 6659Methyl 2-chloroacrylateHCID 129612-MercaptoacetamideHCID 312751,4-Dioxane

Product 1

HCID 198754855-Chloro-5-methoxycarbonyl-3-thiapentanamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Mercaptoacetamide (18.79 g) was stirred in a mixture of dry 1,4-dioxan (200 ml) and dry pyridine (33.5 ml)) whilst methyl 2-chloroacrylate (24.88 g) was added dropwise over 15 minutes. The mixture was stirred for 1 hour then stood overnight. The resultant mixture contained the title compound.

Workup

  1. additionwas added dropwise over 15 minutes
  2. waitthen stood overnight

Sources & evidence

ORD record
ord-7ee7a85c10d545b4b1ed1df425ca1296
Source dataset
uspto-grants-1992_10
Patent number
US05153330

Linked notes

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