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

HRID 1105836Notes

Reaction equation

HRID 1105836 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-67c4733968bf44a7a1728434d4e6374c
Source dataset
uspto-grants-1982_01
Patent number
US04310537

Reaction notes

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