Water → Ethyl 3-isothiocyanatopyrrolidine-1-carboxylate

HRID 1460508Notes

Reaction equation

HRID 1460508 reaction equation
[C:1](Cl)(Cl)=[S:2].O.[NH2:6][CH:7]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:8]1.C(=O)([O-])[O-].[Ca+2]>ClC(Cl)Cl>[N:6]([CH:7]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:8]1)=[C:1]=[S:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10040ThiophosgeneHCID 10112Calcium CarbonateHCID 13656208Ethyl 3-aminopyrrolidine-1-carboxylate

Product 1

HCID 14575268Ethyl 3-isothiocyanatopyrrolidine-1-carboxylateYield 69.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

a-1) To a stirred mixture of 25 parts of carbonothioic dichloride, 65 parts of water and 210 parts of trichloromethane were added dropwise 9.3 parts of ethyl 3-aminopyrrolidinecarboxylate. Upon completion, the reaction mixture was stirred for 15 minutes at room temperature. 10.7 Parts of calcium carbonate were added portionwise during a period of 10 minutes and stirring was continued overnight at room temperature. The reaction mixture was filtered and the separated organic layer was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated. The residue was distilled at 6.65 Pa, yielding 7.5 parts (69.3%) of ethyl 3-isothiocyanato-1-pyrrolidinecarboxylate; bp. 101° C. (interm 6).

Workup

  1. stirringstirring
  2. waitwas continued overnight at room temperature
  3. filtrationThe reaction mixture was filtered
  4. customthe separated organic layer was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. distillationThe residue was distilled at 6.65 Pa

Sources & evidence

ORD record
ord-8d3dc511e3eb4d6490b335eacd686259
Source dataset
uspto-grants-1991_12
Patent number
US05071846

Reaction notes

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