Diphosgene → Methyl 4-isocyanato-3-methylbenzoate

HRID 551178Notes

Reaction equation

HRID 551178 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-23916c756af34efea3e9d2f190a05587
Source dataset
uspto-grants-2011_05
Patent number
US07947700B2

Reaction notes

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