Felbinac → N-methoxy-N-methyl-4-biphenylacetamide

HRID 924928노트

반응식

HRID 924928 반응식
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8](O)=[O:9])=[CH:3][CH:2]=1.Cl.[CH3:18][NH:19][O:20][CH3:21].Cl.CN(C)CCCN=C=NCC.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C>ClCCl>[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8]([N:19]([O:20][CH3:21])[CH3:18])=[O:9])=[CH:3][CH:2]=1

참가 물질

7

반응물 5

HCID 3332Felbinac2회HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, 화합물

생성물 1

HCID 17815837N-methoxy-N-methyl-4-biphenylacetamide수율 83.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 2-(biphenyl-4-yl)acetic acid (1 g, 4.7 mmol), N,O-dimethylhydroxylamine hydrochloride (458 mg, 4.7 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (900 g, 4.7 mmol), hydroxybenzotriazole (635 mg, 4.7 mmol), and triethylamine (1.42 g, 14.1 mmol) in dichloromethane (30 mL) was stirred at room temperature overnight. When TLC indicated that 2-(biphenyl-4-yl)acetic acid was consumed, the reaction mixture was diluted with water (30 mL), and extracted with EtOAc (30 mL×3). The combined organic layer was dried over Na2SO4, concentrated in vacuo, and purified by column chromatography (PE:EtOAc=8:1) to afford 2-(biphenyl-4-yl)-N-methoxy-N-methylacetamide (1.0 g, yield 83%).

후처리

  1. customwas consumed
  2. additionthe reaction mixture was diluted with water (30 mL)
  3. extractionextracted with EtOAc (30 mL×3)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography (PE:EtOAc=8:1)

출처 및 근거

ORD 기록
ord-e396328a60ad4d90a4e19fc9fe2e92b4
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09283229B2

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