Diphosgene → Methyl 4-isocyanato-3-methylbenzoate

HRID 1629823Notes

Reaction equation

HRID 1629823 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].Cl[C:14]([O:17]C(Cl)=O)(Cl)Cl>O1CCOCC1>[N:1]([C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12])=[C:14]=[O:17]

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 2736799Methyl 4-amino-3-methylbenzoate

Product 1

HCID 86069399Methyl 4-isocyanato-3-methylbenzoate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.50 g (9.08 mmol) methyl 4-amino-3-methyl-benzoate are dissolved in 250 ml dioxane combined with 1.3 ml (10.7 mmol) trichloromethyl-chloroformate and refluxed for 5.5 hours with stirring. Then the mixture is evaporated down i. vac. and the residue is further reacted without any more purification.

Workup

  1. temperaturerefluxed for 5.5 hours
  2. customThen the mixture is evaporated down i
  3. customand the residue is further reacted without any more purification

Sources & evidence

ORD record
ord-53c5e69722cf4c0698adead11168e5a2
Source dataset
uspto-grants-2014_07
Patent number
US08791103B2

Reaction notes

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