p-Toluenesulfonic acid → N,N'-Bismethoxycarbonyl-N"-(5-phenoxysulfonyl-2-ureidophenyl)guanidine

HRID 2164407Notes

Reaction equation

HRID 2164407 reaction equation
[O:1]([S:8]([C:11]1[CH:12]=[CH:13][C:14]([NH:18][C:19]([NH2:21])=[O:20])=[C:15]([CH:17]=1)[NH2:16])(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][O:23][C:24]([NH:26][C:27](=[N:30][C:31]([O:33][CH3:34])=[O:32])SC)=[O:25].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C(OCC)(=O)C>[CH3:34][O:33][C:31]([NH:30][C:27]([NH:26][C:24]([O:23][CH3:22])=[O:25])=[N:16][C:15]1[CH:17]=[C:11]([S:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)(=[O:9])=[O:10])[CH:12]=[CH:13][C:14]=1[NH:18][C:19]([NH2:21])=[O:20])=[O:32]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 155855265-Phenoxysulfonyl-2-ureidoaniline

Product 1

HCID 136068114N,N'-Bismethoxycarbonyl-N"-(5-phenoxysulfonyl-2-ureidophenyl)guanidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

15.3 g of 5-phenoxysulfonyl-2-ureidoaniline, 12 g of N,N'-bismethoxycarbonyl-S-methylisothiourea and 100 mg of p-toluenesulfonic acid in 80 ml of methanol and 80 ml of ethyl acetate are stirred under reflux for four hours. After cooling down, the solid is filtered off with suction and washed with ethyl acetate and diisopropyl ether. For recrystallization, the solid is dissolved in dimethylformamide at about 50° C., treated with active charcoal, filtered, ethyl acetate and diisopropyl ether are added and crystallization is allowed to occur, melting point 193° C., decomposition.

Workup

  1. temperatureunder reflux for four hours
  2. temperatureAfter cooling down
  3. filtrationthe solid is filtered off with suction
  4. washwashed with ethyl acetate and diisopropyl ether
  5. customFor recrystallization
  6. dissolutionthe solid is dissolved in dimethylformamide at about 50° C.
  7. additiontreated with active charcoal
  8. filtrationfiltered
  9. additionethyl acetate and diisopropyl ether are added
  10. customcrystallization

Sources & evidence

ORD record
ord-394ed03161414414ade45971d9aadca9
Source dataset
uspto-grants-1985_03
Patent number
US04504490

Reaction notes

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