p-Toluenesulfonic acid → HCID 178502525, compound

HRID 2164415Notes

Reaction equation

HRID 2164415 reaction equation
[C:1]([NH:4][C:5](=[O:28])[NH:6][C:7]1[CH:13]=[CH:12][C:11]([O:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)(=[O:17])=[O:16])=[CH:10][C:8]=1[NH2:9])(=[O:3])[CH3:2].[CH3:29][O:30][C:31]([NH:33][C:34](=[N:37][C:38]([O:40][CH3:41])=[O:39])SC)=[O:32].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[C:1]([NH:4][C:5](=[O:28])[NH:6][C:7]1[CH:13]=[CH:12][C:11]([O:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:25])[F:27])[CH:19]=2)(=[O:16])=[O:17])=[CH:10][C:8]=1[NH:9][C:34]([NH:37][C:38]([O:40][CH3:41])=[O:39])=[N:33][C:31]([O:30][CH3:29])=[O:32])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 155854692-(3-Acetylureido)-5-(3-trifluoromethylphenylsulfonyloxy)aniline

Product 1

HCID 178502525HCID 178502525, compound

Procedure

14.6 g of 2-(3-acetylureido)-5-(3-trifluoromethylphenylsulfonyloxy)aniline, 12.4 g of N,N'-bismethoxycarbonyl-S-methylisothiourea and 75 mg of p-toluenesulfonic acid are stirred under reflux for two hours. After cooling down, the mixture is evaporated under reduced pressure, the residue is recrystallized from isopropanol and the crystals are stirred with cold ethyl acetate, filtered off with suction and washed, melting point 189° C., decomposition.

Workup

  1. temperatureunder reflux for two hours
  2. temperatureAfter cooling down
  3. customthe mixture is evaporated under reduced pressure
  4. customthe residue is recrystallized from isopropanol
  5. filtrationfiltered off with suction
  6. washwashed

Sources & evidence

ORD record
ord-696cca6d470e43d4b52233793f0e00df
Source dataset
uspto-grants-1985_03
Patent number
US04504490

Reaction notes

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