Benzoyl chloride → Methyl 2-phenyl-benzoxazole-6-carboxylate

HRID 2362038Notes

Reaction equation

HRID 2362038 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[OH:12].[C:13](Cl)(=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCOCC1.C(Cl)Cl>[C:14]1([C:13]2[O:12][C:3]3[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][C:2]=3[N:1]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 7020619Benzoic acid, 4-amino-3-hydroxy-, methyl ester

Product 1

HCID 10586965Methyl 2-phenyl-benzoxazole-6-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
210 °C

Procedure

A mixture of methyl 4-amino-3-hydroxy-benzoate is (0.3 g, 1.8 mmol) and benzoyl chloride It (0.23 mL, 2.0 mmol) in dioxane (2.5 mL) was heated at 210° C. under microwave for 15 min. The reaction mixture was diluted with CH2Cl2 and washed with aq. NaHCO3. The organic solution was dried over Na2SO4, concentrated and purified by flash column chromatography (silica gel, 20% EtOAc/heptane) to give 1u (0.39 g).

Workup

  1. washwashed with aq. NaHCO3
  2. dry with materialThe organic solution was dried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by flash column chromatography (silica gel, 20% EtOAc/heptane)

Sources & evidence

ORD record
ord-1e26e80f0ae14513ad1ffb7239af1fc0
Source dataset
uspto-grants-2014_04
Patent number
US08691805B2

Reaction notes

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