Hydrochloric Acid → Ethyl 3-[[[(2-aminophenyl)amino]thioxomethyl]amino]-1-pyrrolidinecarboxylate

HRID 704707Notes

Reaction equation

HRID 704707 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]([NH:13][CH:14]1[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15]1)=[S:12])([O-])=O.[Cl-].[NH4+].CO.Cl>[Fe].O>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]([NH:13][CH:14]1[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15]1)=[S:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 25517Ammonium ChlorideHCID 15037311Ethyl 3-[[[(2-nitrophenyl)amino]thioxomethyl]amino]-1-pyrrolidinecarboxylate

Product 1

HCID 15037312Ethyl 3-[[[(2-aminophenyl)amino]thioxomethyl]amino]-1-pyrrolidinecarboxylateYield 97.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of 34 parts of ethyl 3-[[[(2-nitrophenyl)amino]thioxomethyl]amino]-1-pyrrolidinecarboxylate, 56 parts of iron-powder, 2 parts of ammonium chloride, 160 parts of methanol and 30 parts of water was stirred and acidified with hydrochloric acid. Stirring was continued for 2 hours at reflux temperature. The reaction mixture was filtered over diatomaceous earth and the filtrate was evaporated, yielding 30 parts (97.5%) of ethyl 3-[[[(2-aminophenyl)amino]thioxomethyl]amino]-1-pyrrolidinecarboxylate as a residue (interm. 23).

Workup

  1. stirringStirring
  2. temperatureat reflux temperature
  3. filtrationThe reaction mixture was filtered over diatomaceous earth
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-2471696767074a4591a692a4b10283f5
Source dataset
uspto-grants-1991_01
Patent number
US04988689

Reaction notes

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