Methyl chloroformate → 1-(3-Methoxycarbonyl-2-thioureido)-5-phenylsulfinyl-2-nitrobenzene

HRID 616116Notes

Reaction equation

HRID 616116 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([S:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])[CH:5]=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].[CH3:19][O:20][C:21]([N:23]=[C:24]=[S:25])=[O:22].[S-]C#N.[K+].COC(Cl)=O>CC(C)=O>[CH3:19][O:20][C:21]([NH:23][C:24](=[S:25])[NH:1][C:2]1[CH:7]=[C:6]([S:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])[CH:5]=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17])=[O:22]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 516872Potassium thiocyanateHCID 552246Methoxycarbonyl isothiocyanateHCID 130355725-(Benzenesulfinyl)-2-nitroaniline

Product 1

HCID 203710171-(3-Methoxycarbonyl-2-thioureido)-5-phenylsulfinyl-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A suspension of 5.2 g. of 1-amino-5-phenylsulfinyl-2-nitrobenzene in 50 ml. of acetone is treated at 20°-25° C with a solution of 100 ml. of methoxycarbonyl isothiocyanate (made from 0.125 mol. (each) of potassium thiocyanate and methylchloroformate) in acetone. After several days, the solvent is stripped off under vacuum and the residue triturated with ether. Recrystallization of the crude product from methanol-chloroform yields 1-(3-methoxycarbonyl-2-thioureido)-5-phenylsulfinyl-2-nitrobenzene.

Workup

  1. additionA suspension of 5.2 g
  2. waitAfter several days
  3. customthe residue triturated with ether
  4. customRecrystallization of the crude product from methanol-chloroform

Sources & evidence

ORD record
ord-24c8f623c81f489597ddaec554bbdc15
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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