2-Nitrophenyl isothiocyanate → Ethyl 3-[[[(2-nitrophenyl)amino]thioxomethyl]amino]-1-pyrrolidinecarboxylate

HRID 1886391Notes

Reaction equation

HRID 1886391 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3]1.[N:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22])=[C:13]=[S:14]>O1CCCC1>[N+:21]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[NH:12][C:13]([NH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3]1)=[S:14])([O-:23])=[O:22]

Participants

4

Reactant 2

HCID 1376902-Nitrophenyl isothiocyanateHCID 13656208Ethyl 3-aminopyrrolidine-1-carboxylate

Product 1

HCID 15037311Ethyl 3-[[[(2-nitrophenyl)amino]thioxomethyl]amino]-1-pyrrolidinecarboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 15.8 parts of ethyl 3-amino-1-pyrrolidinecarboxylate, 18 parts of 1-isothiocyanato-2-nitrobenzene and 180 parts of tetrahydrofuran was stirred for 1 hour at room temperature. The reaction mixture was evaporated, yielding 34 parts (100%) of ethyl 3-[[[(2-nitrophenyl)-amino]thioxomethyl]amino]-1-pyrrolidinecarboxylate as a residue (int. 22).

Workup

  1. customThe reaction mixture was evaporated

Sources & evidence

ORD record
ord-5594102111fe454ba2376e7050f7d760
Source dataset
uspto-grants-1992_09
Patent number
US05151424

Reaction notes

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