Trimethyl orthobeznoate → 6-Chloro-2-phenyl-benzoxazole-4-carboxylic acid

HRID 506228

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HRID 506228 반응식
[NH2:1][C:2]1[C:10]([OH:11])=[CH:9][C:8]([Cl:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CO[C:15](OC)(OC)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>>[Cl:12][C:8]1[CH:9]=[C:10]2[O:11][C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:1][C:2]2=[C:3]([C:4]([OH:6])=[O:5])[CH:7]=1

참가 물질

4

반응물 3

HCID 69720Trimethyl orthobeznoateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 180011182-Amino-5-chloro-3-hydroxybenzoic acid

생성물 1

HCID 684576406-Chloro-2-phenyl-benzoxazole-4-carboxylic acid수율 33.5%

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온도
90 °C

실험 절차

A 25-mL, round bottomed flask equipped with a magnetic stirrer was charged with 2-amino-5-chloro-3-hydroxybenzoic acid (0.931 g, 4.96 mmol), trimethyl orthobenzoate (7.23 g, 39.7 mmol), and pyridinium p-toluenesulfonate (0.062 g, 0.248 mmol). After stirring at 90° C. for 1 h, the reaction was diluted with hexanes (30 mL) filtered, and the filter cake dried in a vacuum oven at 40° C. to afford 0.455 g (33% yield) of 6-chloro-2-phenyl-benzoxazole-4-carboxylic acid as a brown solid: 1H NMR (500 MHz, DMSO-d6) δ 8.24 (m, 3H), 7.84 (s, 1H), 7.65 (m, 3H); MS (ESI) m/z 272 (M−H).

후처리

  1. customA 25-mL, round bottomed flask equipped with a magnetic stirrer
  2. filtrationfiltered
  3. customthe filter cake dried in a vacuum oven at 40° C.

출처 및 근거

ORD 기록
ord-4630638cd837403eb3c4a7e93e3d38ae
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781430B2

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