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

HRID 409924
Notes
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Reaction equation

HRID 409924 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 25a (0.3 g, 1.8 mmol) and benzoyl chloride 25b (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 25c (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-587702ed850f48d095c6c1f8c42e9670
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08759533B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes