Benzocaine → Ethyl 4-isocyanatobenzoate

HRID 1092352Notes

Reaction equation

HRID 1092352 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)[CH3:2].Cl[C:14](OC(Cl)(Cl)Cl)=[O:15]>C1COCC1>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:14]=[O:15])=[CH:7][CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 10426Diphosgene

Product 1

HCID 589805Ethyl 4-isocyanatobenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.5 g (9.08 mmol) 4-amino-benzoic acid ethyl ester in 16 ml of THF was added 0.621 ml (5 mmol) of trichloromethyl chloroformate. The reaction mixture was stirred under reflux for 1 h and then concentrated under reduced pressure to dryness. The crude 4-Isocyanato-benzoic acid ethyl ester was used in the next step.

Workup

  1. temperatureunder reflux for 1 h
  2. concentrationconcentrated under reduced pressure to dryness

Sources & evidence

ORD record
ord-6524238699d842e4802ab3497a077a82
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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