Diphosgene → Methyl 4-isocyanato-3-methylbenzoate

HRID 2222477Notes

Reaction equation

HRID 2222477 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
  2. customThen the mixture is evaporated down i
  3. customand the residue is further reacted without any more purification

Sources & evidence

ORD record
ord-eac8a00cb516434c9f3ddba03c66a420
Source dataset
uspto-grants-2008_05
Patent number
US07371743B2

Reaction notes

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