Phosgene → 3-(Methylthio)phenyl isocyanate

HRID 2071533Notes

Reaction equation

HRID 2071533 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[C:10](Cl)(Cl)=[O:11]>C(COC)OC>[CH3:9][S:8][C:4]1[CH:3]=[C:2]([N:1]=[C:10]=[O:11])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6371Phosgene2×HCID 15693Benzenamine, 3-(methylthio)-

Product 1

HCID 1414183-(Methylthio)phenyl isocyanate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

m-Aminothioanisole (27.8 g., 0.2 mole) in 100 ml dry dimethoxyethane is added to a saturated solution of phosgene in 200 ml dry dimethoxyethane. Phosgene is passed into the refluxing mixture for a further 4 hr. and then the mixture is heated under nitrogen for 21 hours. Solvent is removed in vacuo to afford m-methylthiophenyl isocyanate as an amber oil which is dissolved in benzene for use in the next step.

Workup

  1. temperatureand then the mixture is heated under nitrogen for 21 hours
  2. customSolvent is removed in vacuo

Sources & evidence

ORD record
ord-f40c891b94de444c960426457b392291
Source dataset
uspto-grants-1977_09
Patent number
US04046909

Reaction notes

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