Water → (1-Phenylcyclopentylmethyl)isothiocyanate

HRID 1855740Notes

Reaction equation

HRID 1855740 reaction equation
[OH-].[Na+].O.[C:4]1([C:10]2([CH2:15][NH2:16])[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:17](=S)=[S:18]>>[C:4]1([C:10]2([CH2:15][N:16]=[C:17]=[S:18])[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6348Carbon DisulfideHCID 14798Sodium HydroxideHCID 205131(1-Phenylcyclopentyl)methanamine

Product 1

HCID 23348553(1-Phenylcyclopentylmethyl)isothiocyanate

Procedure

A solution of 20 parts of sodium hydroxide and 300 parts of water is cooled to ±10° C. and there are added successively 41.8 parts of carbon disulfide and then dropwise 95 parts of 1-phenyl-cyclopentylmethylamine (exothermic reaction). Upon completion, the cooling-bath is removed and the whole is stirred at 30 minutes at room temperature. Then there are added dropwise at 30° C., 54.25 parts of ethyl chloroformate (exothermic reaction: cooling is necessary). The whole is stirred for 3 hours 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, yielding 86 parts of (1-phenylcyclopentylmethyl)isothiocyanate; bp. 125° C. at 0.2 mm pressure; nD20 :1.5848; d2020 :1.0910.

Workup

  1. customto ±10° C.
  2. customUpon completion, the cooling-bath is removed
  3. additionThen there are added dropwise at 30° C.
  4. stirringThe whole is stirred for 3 hours at 50° C
  5. temperatureThe reaction mixture is cooled
  6. extractionthe product is extracted with benzene
  7. customThe extract is dried
  8. filtrationfiltered
  9. customevaporated
  10. distillationThe oily residue is distilled

Sources & evidence

ORD record
ord-de51a315ed51481f9e93d60376540b76
Source dataset
uspto-grants-1980_08
Patent number
US04216217

Reaction notes

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