Methoxycarbonyl isothiocyanate → 1,2-Bis(3-methoxycarbonyl-2-thioureido)-4-methylthiomethoxybenzene

HRID 616107Notes

Reaction equation

HRID 616107 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][S:10][CH3:11])=[CH:4][C:3]=1[NH2:12].[CH3:13][O:14][C:15]([N:17]=[C:18]=[S:19])=[O:16]>CC(C)=O>[CH3:13][O:14][C:15]([NH:17][C:18](=[S:19])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][S:10][CH3:11])=[CH:4][C:3]=1[NH:12][C:18]([NH:17][C:15]([O:14][CH3:13])=[O:16])=[S:19])=[O:16]

Participants

4

Reactant 2

HCID 552246Methoxycarbonyl isothiocyanateHCID 203628424-[(Methylsulfanyl)methoxy]benzene-1,2-diamine

Product 1

HCID 203710021,2-Bis(3-methoxycarbonyl-2-thioureido)-4-methylthiomethoxybenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The 1,2-diamino-4-methylthiomethoxybenzene prepared above is dissolved in 60 ml. acetone and treated overnight with 6 g. methoxycarbonyl isothiocyanate at room temperature. The mixture is concentrated and the residue stirred with 500 ml. water and the brown solid filtered off. The residue is extracted with 250 ml. dichloromethane, filtered, treated with charcoal, and recrystallized from dichloromethanebenzene to afford 1,2-bis(3-methoxycarbonyl-2-thioureido)-4-methylthiomethoxybenzene.

Workup

  1. dissolutionis dissolved in 60 ml
  2. customat room temperature
  3. concentrationThe mixture is concentrated
  4. filtrationwater and the brown solid filtered off
  5. extractionThe residue is extracted with 250 ml
  6. filtrationdichloromethane, filtered
  7. additiontreated with charcoal
  8. customrecrystallized from dichloromethanebenzene

Sources & evidence

ORD record
ord-0d11de04ce33462ca3515167d02c7b58
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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