N1-[(5-methyl-2-furanyl)methyl]-1,2-benzenediamine → Ethyl 3-[[[[2-[[(5-methyl-2-furanyl)methyl]amino]phenyl]amino]thioxomethyl]amino]-1-pyrrolidinecarboxylate

HRID 704705Notes

Reaction equation

HRID 704705 reaction equation
[N:1]([CH:4]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5]1)=[C:2]=[S:3].[CH3:14][C:15]1[O:19][C:18]([CH2:20][NH:21][C:22]2[C:23]([NH2:28])=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:17][CH:16]=1>O1CCCC1>[CH3:14][C:15]1[O:19][C:18]([CH2:20][NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[NH:28][C:2]([NH:1][CH:4]2[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5]2)=[S:3])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 14182882N1-[(5-methyl-2-furanyl)methyl]-1,2-benzenediamineHCID 14575268Ethyl 3-isothiocyanatopyrrolidine-1-carboxylate

Product 1

HCID 15037310Ethyl 3-[[[[2-[[(5-methyl-2-furanyl)methyl]amino]phenyl]amino]thioxomethyl]amino]-1-pyrrolidinecarboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 80 parts of ethyl 3-isothiocyanato-1-pyrrolidinecarboxylate, 88.8 parts of N1 -[(5-methyl-2-furanyl)methyl]-1,2-benzenediamine and 560 parts of tetrahydrofuran was stirred for 2 hours at reflux temperature. After cooling to room temperature, the reaction mixture was evaporated, yielding 144.9 parts (100%) of ethyl 3-[[[[2-[[(5-methyl-2-furanyl)methyl]amino]phenyl]amino]thioxomethyl]amino]-1-pyrrolidinecarboxylate as a residue (interm. 7).

Workup

  1. temperatureat reflux temperature
  2. customthe reaction mixture was evaporated

Sources & evidence

ORD record
ord-fe57936b56c343ee9c2a26f578ca01e4
Source dataset
uspto-grants-1991_01
Patent number
US04988689

Reaction notes

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