Diisopropyl Ether → 1-Methoxycarbonyl-3-[5-(3-trifluoromethylphenylsulfonyloxy)-2-ureidophenyl]thiourea

HRID 2164413Notes

Reaction equation

HRID 2164413 reaction equation
[CH3:1][O:2][C:3]([N:5]=[C:6]=[S:7])=[O:4].[F:8][C:9]([F:32])([F:31])[C:10]1[CH:11]=[C:12]([S:16]([O:19][C:20]2[CH:21]=[CH:22][C:23]([NH:27][C:28]([NH2:30])=[O:29])=[C:24]([CH:26]=2)[NH2:25])(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1.C(OC(C)C)(C)C>O1CCOCC1>[CH3:1][O:2][C:3]([NH:5][C:6]([NH:25][C:24]1[CH:26]=[C:20]([O:19][S:16]([C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([C:9]([F:8])([F:31])[F:32])[CH:11]=2)(=[O:18])=[O:17])[CH:21]=[CH:22][C:23]=1[NH:27][C:28]([NH2:30])=[O:29])=[S:7])=[O:4]

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 552246Methoxycarbonyl isothiocyanateHCID 155854705-(3-Trifluoromethylphenylsulfonyloxy)-2-ureidoaniline

Product 1

HCID 155854441-Methoxycarbonyl-3-[5-(3-trifluoromethylphenylsulfonyloxy)-2-ureidophenyl]thiourea

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

12 ml of methoxycarbonyl isothiocyanate are added dropwise, with stirring, to 18.7 g of 5-(3-trifluoromethylphenylsulfonyloxy)-2-ureidoaniline in 300 ml of dioxane, the temperature rising to about 40° C. The mixture is stirred for a further four hours without cooling, 60 ml of diisopropyl ether are added and the precipitate is filtered off with suction. After washing with diisopropyl ether, recrystallization is carried out from methanol/diisopropyl ether with the addition of active charcoal, melting point 190° C., decomposition.

Workup

  1. customrising to about 40° C
  2. temperaturewithout cooling
  3. filtrationthe precipitate is filtered off with suction
  4. washAfter washing with diisopropyl ether, recrystallization
  5. additionis carried out from methanol/diisopropyl ether with the addition of active charcoal, melting point 190° C., decomposition.

Sources & evidence

ORD record
ord-8819df7b0fb749bf826747c9838a7746
Source dataset
uspto-grants-1985_03
Patent number
US04504490

Reaction notes

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