p-Toluenesulfonic acid → N,N'-Bismethoxycarbonyl-N"-[5-(3-trifluoromethylphenylsulfonyloxy)-2-ureidophenyl]guanidine

HRID 2164414Notes

Reaction equation

HRID 2164414 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([S:9]([O:12][C:13]2[CH:14]=[CH:15][C:16]([NH:20][C:21]([NH2:23])=[O:22])=[C:17]([CH:19]=2)[NH2:18])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[CH3:26][O:27][C:28]([NH:30][C:31](=[N:34][C:35]([O:37][CH3:38])=[O:36])SC)=[O:29].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)(=O)C.CO>[CH3:38][O:37][C:35]([NH:34][C:31]([NH:30][C:28]([O:27][CH3:26])=[O:29])=[N:18][C:17]1[CH:19]=[C:13]([O:12][S:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:24])([F:1])[F:25])[CH:4]=2)(=[O:11])=[O:10])[CH:14]=[CH:15][C:16]=1[NH:20][C:21]([NH2:23])=[O:22])=[O:36]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 155854705-(3-Trifluoromethylphenylsulfonyloxy)-2-ureidoaniline

Product 1

HCID 135999370N,N'-Bismethoxycarbonyl-N"-[5-(3-trifluoromethylphenylsulfonyloxy)-2-ureidophenyl]guanidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

12.5 g of 5-(3-trifluoromethylphenylsulfonyloxy)-2-ureidoaniline, 13.6 g of N,N'-bismethoxycarbonyl-S-methylisothiourea and 100 mg of p-toluenesulfonic acid in 90 ml of ethyl acetate and 45 ml of methanol are stirred under reflux for 20 minutes. After cooling down, the mixture is evaporated to dryness under reduced pressure, and the residue is stirred with diisopropyl ether and filtered off with suction. Recrystallization from ethyl acetate/diisopropyl ether, melting point 131° C.

Workup

  1. temperatureunder reflux for 20 minutes
  2. temperatureAfter cooling down
  3. customthe mixture is evaporated to dryness under reduced pressure
  4. filtrationfiltered off with suction
  5. customRecrystallization from ethyl acetate/diisopropyl ether, melting point 131° C.

Sources & evidence

ORD record
ord-11000bbcc7fb485aa61f5b15f7ed30ef
Source dataset
uspto-grants-1985_03
Patent number
US04504490

Reaction notes

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