Methoxycarbonyl isothiocyanate → 3-(3-Acetylthioureido)-4-(3-carbomethoxythioureido)benzophenone

HRID 1439784Notes

Reaction equation

HRID 1439784 reaction equation
[C:1]([NH:4][C:5](=[S:22])[NH:6][C:7]1[CH:8]=[C:9]([CH:18]=[CH:19][C:20]=1[NH2:21])[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11])(=[O:3])[CH3:2].[C:23]([N:27]=[C:28]=[S:29])([O:25][CH3:26])=[O:24]>CC(C)=O>[C:1]([NH:4][C:5](=[S:22])[NH:6][C:7]1[CH:8]=[C:9]([CH:18]=[CH:19][C:20]=1[NH:21][C:28]([NH:27][C:23]([O:25][CH3:26])=[O:24])=[S:29])[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 552246Methoxycarbonyl isothiocyanateHCID 130231783-(3-Acetylthioureido)-4-aminobenzophenone

Product 1

HCID 130231803-(3-Acetylthioureido)-4-(3-carbomethoxythioureido)benzophenoneYield 40%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 3-(3-acetylthioureido)-4-aminobenzophenone (1.1 g.) in acetone (15 ml.) is added carbomethoxy isothiocyanate (0.41 g.). The mixture is heated to reflux and then is stirred at room temperature for 18 hours. The crude product is collected by filtration, washed with acetone and ether and then dried to afford 0.6 g. (40% yield) of 3-(3-acetylthioureido)-4-(3-carbomethoxythioureido)benzophenone, m.p. 203°-204° C., dec.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. filtrationThe crude product is collected by filtration
  4. washwashed with acetone and ether
  5. customdried
  6. customto afford 0.6 g

Sources & evidence

ORD record
ord-4239f7f648e44c1899f83fe1d5c635c4
Source dataset
uspto-grants-1977_11
Patent number
US04060636

Reaction notes

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