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

HRID 2365593Notes

Reaction equation

HRID 2365593 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-carboxylateYield 85.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
210 °C

Procedure

A mixture of methyl 4-amino-3-hydroxy-benzoate 1s (0.3 g, 1.8 mmol) and benzoyl chloride 1t (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-5da625cebf324701a7105f7aac27bb65
Source dataset
uspto-grants-2014_04
Patent number
US08697683B2

Reaction notes

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