Water → HCID 23348526, compound

HRID 1855741Notes

Reaction equation

HRID 1855741 reaction equation
[OH-].[K+].O.[S:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]1([CH2:12][NH2:13])[CH2:11][CH2:10]1.ClC(OCC)=O.[C:20](=S)=[S:21]>>[S:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]1([CH2:12][N:13]=[C:20]=[S:21])[CH2:11][CH2:10]1

Participants

6

Reactant 5

HCID 962WaterHCID 6348Carbon DisulfideHCID 10928Ethyl chloroformateHCID 14797Potassium HydroxideHCID 156111751-[1-(Thiophen-2-yl)cyclopropyl]methanamine

Product 1

HCID 23348526HCID 23348526, compound

Procedure

A solution of 11 parts of potassium hydroxide in 200 parts of water is cooled to about 10° C. and there are added successively 22.8 parts of carbon disulfide and then dropwise 42 parts of 1-(2-thienyl)cyclopropylmethylamine (exothermic reaction). Upon completion, the whole is stirred for 30 minutes at room temperature. Then there are added at 30° C., 29.8 parts of ethyl chloroformate (exothermic reaction: cooling is necessary). The whole is stirred for 3 hours while heating at 50° C. The reaction mixture is cooled and the product is extracted with benzene. The extract is dried, filtered and evaporated. The oily residue is distilled twice, yielding 40 parts of [1-(2-thienyl)cyclopropylmethyl]isothiocyanate; bp. 140°-150° C. at 10 mm pressure; nD20 :1.6008; d2020 :1.1911.

Workup

  1. additionThen there are added at 30° C.
  2. stirringThe whole is stirred for 3 hours
  3. temperaturewhile heating at 50° C
  4. temperatureThe reaction mixture is cooled
  5. extractionthe product is extracted with benzene
  6. customThe extract is dried
  7. filtrationfiltered
  8. customevaporated
  9. distillationThe oily residue is distilled twice

Sources & evidence

ORD record
ord-1edbcd7f3a5c415190ae3dd4a84c019f
Source dataset
uspto-grants-1980_08
Patent number
US04216217

Reaction notes

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