Methyl chloroformate → 2-Nitro-4-phenylsulfinyl-1-(3-methoxycarbonyl-2-thioureido)benzene

HRID 616140Notes

Reaction equation

HRID 616140 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([S:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[CH3:19][O:20][C:21]([N:23]=[C:24]=[S:25])=[O:22].[S-]C#N.[K+].COC(Cl)=O>CC(C)=O>[N+:1]([C:4]1[CH:10]=[C:9]([S:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])[CH:8]=[CH:7][C:5]=1[NH:6][C:24]([NH:23][C:21]([O:20][CH3:19])=[O:22])=[S:25])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 516872Potassium thiocyanateHCID 552246Methoxycarbonyl isothiocyanateHCID 131666462-Nitro-4-phenylsulfinylaniline

Product 1

HCID 203711422-Nitro-4-phenylsulfinyl-1-(3-methoxycarbonyl-2-thioureido)benzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

2.6 G. of 2-nitro-4-phenylsulfinylaniline is dissolved in 25ml. of acetone and treated at 20°-25° C with 60 ml. of a solution of methoxycarbonyl isothiocyanate (made from 0.075 mol. (each) of potassium thiocyanate and methylchloroformate in acetone). After several days, the solvent is evaporated and the residue triturated with ether. Recrystallization from methanol-chloroform yields 2-nitro-4-phenylsulfinyl-1-(3-methoxycarbonyl-2-thioureido)benzene.

Workup

  1. waitAfter several days
  2. customthe solvent is evaporated
  3. customthe residue triturated with ether
  4. customRecrystallization from methanol-chloroform

Sources & evidence

ORD record
ord-c8bcf54ac2974250bf7de2c28022ab16
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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