Phosgene → 3-(Methylthio)phenyl isocyanate

HRID 1973961Notes

Reaction equation

HRID 1973961 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-ed53a967fa7541388177e33edc724727
Source dataset
uspto-grants-1976_12
Patent number
US03998958

Reaction notes

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