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ChemicalBook CAS DataBase List METHYL 4-ISOCYANATOBENZOATE 98
23138-53-6

METHYL 4-ISOCYANATOBENZOATE 98 synthesis

7synthesis methods
-

Yield: 96%

Reaction Conditions:

in 1,4-dioxane for 8 h;Reflux;

Steps:

5.2.1. Compound 1a
To methyl 4-aminobenzoate (30.23 g; 200 mmol) in anhydrous 1,4-dioxane (500 mL) was added trichloromethyl chloroformate (59.35 g; 300 mmol) dropwise and the reaction mixture was refluxed for 8 h. The solvent was removed on the rotary evaporator to yield 1a as a yellow solid, which was purified by vacuum distillation to give a yellow solid (34 g, 96% yield). IR (neat) νNCO 2268 cm-1. 1H NMR (CDCl3): δ 3.88 (s, 3H), 7.14-7.18 (m, 2H), 7.96-8.02 (m, 2H).

References:

Aravapalli, Sridhar;Lai, Huiguo;Teramoto, Tadahisa;Alliston, Kevin R.;Lushington, Gerald H.;Ferguson, Eron L.;Padmanabhan;Groutas, William C. [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 13,p. 4140 - 4148] Location in patent:experimental part

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