Benzoyl chloride → 7-Benzoxazolecarboxylic acid, 2-phenyl-

HRID 506247Notes

Reaction equation

HRID 506247 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[OH:11].[C:12](Cl)(=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[C:13]1([C:12]2[O:11][C:3]3[C:4]([C:5]([OH:7])=[O:6])=[CH:8][CH:9]=[CH:10][C:2]=3[N:1]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 7412Benzoyl chlorideHCID 684433-Aminosalicylic acid

Product 1

HCID 118067277-Benzoxazolecarboxylic acid, 2-phenyl-Yield 86%

Procedure

2-Phenylbenzoxazole-7-carboxylic acid was prepared from 3-aminosalicyclic acid and benzoyl chloride using a procedure identical to that described in Step A of Example 1. This material was obtained in 86% yield as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 8.30 (dd, J=7.2, 2.1 Hz, 2H), 7.98 (dd, J=12.9, 7.8 Hz, 2H), 7.60 (m, 3H), 7.48 (t, J=7.8 Hz, 1H); MS (APCI) m/z 240 [M+H]+

Workup

  1. customThis material was obtained in 86% yield as an off-white solid

Sources & evidence

ORD record
ord-c78732fb9090415d86cf86518ef28e27
Source dataset
uspto-grants-2010_08
Patent number
US07781430B2

Reaction notes

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