Thionyl Chloride → HCID 57100648, compound

HRID 371118Notes

Reaction equation

HRID 371118 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6](Cl)(Cl)[CH:7]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[S:13])C(=S)N>>[Cl:5][CH:6]=[CH:7][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[S:13]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 53821675HCID 53821675, compound

Product 1

HCID 57100648HCID 57100648, compound

Procedure

Thionyl chloride (25 ml) is dropwise added to the ester (3) (47.6 g). After 30 minutes at 30° C., the mixture is distilled in vacuo (b.p. 104°-105° C./7 mmHg, Yield: 43 g). To the distillate are added benzene (82 ml) and DBU (42 ml), and the mixture is heated under reflux for 1.5 hours. The reaction mixture is washed with water and distilled in vacuo to give methyl vinylthioacetate (4). Yield: 24.7 g, b.p. 59°-65.5° C.4-5 mmHg.

Workup

  1. distillationthe mixture is distilled in vacuo (b.p. 104°-105° C./7 mmHg, Yield: 43 g)
  2. additionTo the distillate are added benzene (82 ml) and DBU (42 ml)
  3. temperaturethe mixture is heated
  4. temperatureunder reflux for 1.5 hours
  5. washThe reaction mixture is washed with water
  6. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-3dcd1132c79d4b5a84ba927001e926d0
Source dataset
uspto-grants-1985_07
Patent number
US04529721

Reaction notes

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