Water → Ethyl 3-isothiocyanatopyrrolidine-1-carboxylate

HRID 1886389Notes

Reaction equation

HRID 1886389 reaction equation
[OH-].[Na+].O.[NH2:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6]1.C(Cl)(=O)OCC.[C:21](=S)=[S:22]>>[N:4]([CH:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6]1)=[C:21]=[S:22]

Participants

6

Reactant 5

HCID 962WaterHCID 6348Carbon DisulfideHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 13656208Ethyl 3-aminopyrrolidine-1-carboxylate

Product 1

HCID 14575268Ethyl 3-isothiocyanatopyrrolidine-1-carboxylateYield 100%

Procedure

a-4) A mixture of 8.6 parts of sodium hydroxide and 120 parts of water was stirred at a temperature below 10° C. and there were added successively 17 parts of carbon disulfide and 35 parts of ethyl 3-amino-1-pyrrolidinecarboxylate. Stirring was continued for 3 hours. Then there were added dropwise 23.5 parts of ethyl carbonochloridate. Upon completion, stirring was continued for 2 hours at 60° C. The reaction mixture was extracted with methylbenzene. The extract was dried, filtered and evaporated, yielding 55 parts (100%) of ethyl 3-isothiocyanato-1-pyrrolidinecarboxylate as a residue (interm. 6).

Workup

  1. stirringStirring
  2. stirringUpon completion, stirring
  3. waitwas continued for 2 hours at 60° C
  4. extractionThe reaction mixture was extracted with methylbenzene
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-be42c01f177c4837980f2e63478c3811
Source dataset
uspto-grants-1992_09
Patent number
US05151424

Reaction notes

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