Ethyl orthoformate → 1,3-Benzoxazole-5-carboxylic acid

HRID 626217

반응식

[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].[CH:12](OCC)(OCC)OCC>>[O:11]1[C:10]2[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=2[N:1]=[CH:12]1

참가 물질

반응물 2

HCID 31214Ethyl orthoformate

HCID 650833-Amino-4-hydroxybenzoic acid

생성물 1

HCID 190067671,3-Benzoxazole-5-carboxylic acid수율 92%

실험 절차

A mixture of 3-amino-4-hydroxybenzoic acid (8.0 g, 1.0 eq) and 60 mL CH(OEt)3 was heated to reflux for 3 h, and then cooled to rt. The remaining CH(OEt)3 was removed under reduced pressure to give the desired product (7.8 g, 92%). 1H NMR (400 MHz, DMSO-d6) δ 13.00 (brs, 1H), 8.85 (s, 1H), 8.30 (s, 1H), 8.03 (d, J=8.8 Hz, 1H), 7.85 (d, J=8.8 Hz, 1H).

후처리

temperaturewas heated
temperatureto reflux for 3 h
customThe remaining CH(OEt)3 was removed under reduced pressure

출처 및 근거

ORD 기록: ord-3328fabf694640e6b5b931e5acca3048
출처 데이터셋: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US09309211B2

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