Triethylamine → Methyl 4-isocyanato-3-methylbenzoate

HRID 1690529Notes

Reaction equation

HRID 1690529 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([CH3:11])[CH:5]=1.Cl[C:14](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl.CCN(CC)CC>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:14]=[O:16])=[C:6]([CH3:11])[CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 2736799Methyl 4-amino-3-methylbenzoate

Product 1

HCID 86069399Methyl 4-isocyanato-3-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In analogy to the procedure described in example 9.1, 4-amino-3-methyl-benzoic acid methyl ester ([18595-14-7]) was reacted with triphosgene in the presence of Et3N in CH2Cl2 under reflux conditions for 14 h to give the title compound as brown solid. MS: m/e=191.1 [M+].

Sources & evidence

ORD record
ord-ba3aa4902c194b83b9af8673fe56a8f8
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

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