Water → 4-Difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid 4-nitrophenyl ester

HRID 2186452노트

반응식

HRID 2186452 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.CN(C)CCCN=C=NCC.[F:23][CH:24]([F:40])[O:25][C:26]1[C:31]2[N:32]=[C:33]([CH2:35][CH3:36])[O:34][C:30]=2[C:29]([C:37](O)=[O:38])=[CH:28][CH:27]=1.O>CN(C)C1C=CN=CC=1.ClCCl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:37]([C:29]2[C:30]3[O:34][C:33]([CH2:35][CH3:36])=[N:32][C:31]=3[C:26]([O:25][CH:24]([F:23])[F:40])=[CH:27][CH:28]=2)=[O:38])=[CH:6][CH:5]=1)([O-:3])=[O:2]

참가 물질

7

반응물 4

HCID 962WaterHCID 9804-NitrophenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22456643HCID 22456643, 화합물

생성물 1

HCID 545360974-Difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid 4-nitrophenyl ester수율 80.7%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

para-Nitrophenol (0.95 g), 4-dimethylaminopyridine (80 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.4 g) were added to a stirred suspension of 4-difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid (1.6 g) in dry dichloromethane (60 ml) under an atmosphere of nitrogen. The reaction mixture was stirred at room temperature for 18 hours. Water (20 ml) was added and the aqueous layer extracted with dichloromethane (400 ml). The organic layer was washed with water (80 ml), separated, dried over magnesium sulphate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 1:4 ethyl acetate/heptane to 1:1:2 ethyl acetate/dichloromethane/heptane afforded the title compound as a pale yellow solid (1.9 g)

후처리

  1. extractionthe aqueous layer extracted with dichloromethane (400 ml)
  2. washThe organic layer was washed with water (80 ml)
  3. customseparated
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customPurification by column chromatography on silica eluting with 1:4 ethyl acetate/heptane to 1:1:2 ethyl acetate/dichloromethane/heptane

출처 및 근거

ORD 기록
ord-0114594b9977408cbf1a918894fd76f9
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06403791B1

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