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

HRID 924928ノート

反応式

HRID 924928 の反応式
[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

参加物

7

反応物 5

HCID 3332Felbinac2 回HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300、化合物

生成物 1

HCID 17815837N-methoxy-N-methyl-4-biphenylacetamide収率 83.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-e396328a60ad4d90a4e19fc9fe2e92b4
出典データセット
uspto-grants-2016_03
特許番号
US09283229B2

反応ノート

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