Water → HCID 23348537, compound

HRID 1855742Notes

Reaction equation

HRID 1855742 reaction equation
[OH-].[Na+].O.[S:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]1([CH2:14][NH2:15])[CH2:13][CH2:12][CH2:11][CH2:10]1.ClC(OCC)=O.[C:22](=S)=[S:23]>>[S:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]1([CH2:14][N:15]=[C:22]=[S:23])[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 5

HCID 962WaterHCID 6348Carbon DisulfideHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 164951441-[1-(Thiophen-2-yl)cyclopentyl]methanamine

Product 1

HCID 23348537HCID 23348537, compound

Procedure

A solution of 21.2 parts of sodium hydroxide in 500 parts of water is cooled to 10° C. and there is added successively 45.6 parts of carbon disulfide and then dropwise 95.83 parts of 1-(2-thienyl)-cyclopentanemethylamine (exothermic reaction). After the addition is complete, the whole is stirred for 30 minutes at room temperature. Then there are added 57.5 parts of ethyl chloroformate at 30° C. (exothermic reaction: cooling is necessary). The whole is stirred for 3 hours at 50° C. and further stirred overnight without heating. The product is extracted with benzene. The extract is dried, filtered and evaporated. The residue is poured onto 350 parts of water and the whole is heated for 3 hours at 80°-90° C. The mixture is cooled and the product is extracted with dichloromethane. The extract is dried, filtered and evaporated. The oily residue is distilled twice, yielding 88 parts of [1-(2-thienyl)cyclopentylmethyl]isothiocyanate; bp. 110° C. at 0.1 mm pressure; nD20 :1.5960; d2020 :1.1743.

Workup

  1. additionAfter the addition
  2. custom(exothermic reaction: cooling is necessary)
  3. stirringThe whole is stirred for 3 hours at 50° C. and further stirred overnight
  4. temperaturewithout heating
  5. extractionThe product is extracted with benzene
  6. customThe extract is dried
  7. filtrationfiltered
  8. customevaporated
  9. additionThe residue is poured onto 350 parts of water
  10. temperaturethe whole is heated for 3 hours at 80°-90° C
  11. temperatureThe mixture is cooled
  12. extractionthe product is extracted with dichloromethane
  13. customThe extract is dried
  14. filtrationfiltered
  15. customevaporated
  16. distillationThe oily residue is distilled twice

Sources & evidence

ORD record
ord-29421ad13992487a9747e93a86cf5509
Source dataset
uspto-grants-1980_08
Patent number
US04216217

Reaction notes

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