Diphosgene → Methyl 4-isocyanato-3-methylbenzoate

HRID 2094254Notes

Reaction equation

HRID 2094254 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-2629f7b66b3a4471a4879c4fcc6a9ab8
Source dataset
uspto-grants-2013_05
Patent number
US08445525B2

Reaction notes

Loading…