(Chlorothio)formyl chloride → HCID 12851882, compound

HRID 1604976Notes

Reaction equation

HRID 1604976 reaction equation
Cl[C:2]([S:4]Cl)=[O:3].[NH2:6]/[C:7](/[CH3:11])=[CH:8]\[C:9]#[N:10]>O1CCCC1>[C:9]([C:8]1[S:4][C:2](=[O:3])[NH:6][C:7]=1[CH3:11])#[N:10]

Participants

4

Reactant 2

HCID 75990(Chlorothio)formyl chlorideHCID 5325263(2Z)-3-Amino-2-butenenitrile

Product 1

HCID 12851882HCID 12851882, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
140 °C

Procedure

40 g of chlorocarbonylsulfenyl chloride were added to a mixture of 25 g of 3-amino-crotononitrile in 700 ml of tetrahydrofuran and the mixture was refluxed for 3 hours after which the solvent was distilled off under reduced pressure. The residue was heated at 140°C for 10 minutes and cooled and then 1N sodium hydroxide was added thereto. The aqueous solution was washed with ethylacetate, acidified with hydrochloric and extracted with ethylacetate. The organic extracts were dried, concentrated to dryness and isopropyl ether was added to obtain 31 g of 5-cyano-4-methyl-4-thiazoline-2-one melting at 180° to 181°C.

Workup

  1. temperaturethe mixture was refluxed for 3 hours after which the solvent
  2. distillationwas distilled off under reduced pressure
  3. temperaturecooled
  4. addition1N sodium hydroxide was added
  5. washThe aqueous solution was washed with ethylacetate
  6. extractionextracted with ethylacetate
  7. customThe organic extracts were dried
  8. concentrationconcentrated to dryness and isopropyl ether
  9. additionwas added

Sources & evidence

ORD record
ord-1309dfc37fe14d7c85458003eb4f0d39
Source dataset
uspto-grants-1976_04
Patent number
US03948925

Reaction notes

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