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

HRID 1023042
Notes
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Reaction equation

HRID 1023042 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-carboxylate

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 1β (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-eb8c8fe77d1a49378d8e469f7a9fafee
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08722658B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes