Methoxycarbonyl isothiocyanate → 1-[2-(3-Acetylureido)-5-phenoxysulfonylphenyl]-3-methoxycarbonylthiourea

HRID 2164408Notes

Reaction equation

HRID 2164408 reaction equation
[C:1]([NH:4][C:5](=[O:24])[NH:6][C:7]1[CH:13]=[CH:12][C:11]([S:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:16])=[O:15])=[CH:10][C:8]=1[NH2:9])(=[O:3])[CH3:2].[CH3:25][O:26][C:27]([N:29]=[C:30]=[S:31])=[O:28]>O1CCOCC1>[C:1]([NH:4][C:5](=[O:24])[NH:6][C:7]1[CH:13]=[CH:12][C:11]([S:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:16])=[O:15])=[CH:10][C:8]=1[NH:9][C:30]([NH:29][C:27]([O:26][CH3:25])=[O:28])=[S:31])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 552246Methoxycarbonyl isothiocyanateHCID 155853842-(3-Acetylureido)-5-phenoxysulfonylaniline

Product 1

HCID 155853851-[2-(3-Acetylureido)-5-phenoxysulfonylphenyl]-3-methoxycarbonylthiourea

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

17.5 g of 2-(3-acetylureido)-5-phenoxysulfonylaniline and 15 ml of methoxycarbonyl isothiocyanate in 150 ml of dioxane are heated at 80° C. for 5 minutes, and then stirring is continued without heating. After slowly cooling down to room temperature, the dioxane is distilled out under reduced pressure. The residue is dissolved in dimethylformamide, the solution is treated with active charcoal and evaporated and then methanol is added. After cooling down, the precipitate is filtered off with suction and washed with methanol and diisopropyl ether. Melting point 215° C., decomposition.

Workup

  1. temperaturewithout heating
  2. distillationthe dioxane is distilled out under reduced pressure
  3. dissolutionThe residue is dissolved in dimethylformamide
  4. additionthe solution is treated with active charcoal
  5. customevaporated
  6. additionmethanol is added
  7. temperatureAfter cooling down
  8. filtrationthe precipitate is filtered off with suction
  9. washwashed with methanol and diisopropyl ether

Sources & evidence

ORD record
ord-c789a8dbaaaa4effbd53aff75238dd3a
Source dataset
uspto-grants-1985_03
Patent number
US04504490

Reaction notes

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