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2-Ethyl-4-methoxy-3-methylbenzoic acid → N'-(2-(3,5-Difluorophenyl)-2-hydroxyacetyl)-2-ethyl-4-methoxy-3-methylbenzohydrazide

HRID 1037748
ノート
印刷プレビュー

反応式

HRID 1037748 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:14])[C:10]([NH:12][NH2:13])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.[CH2:15]([C:17]1[C:25]([CH3:26])=[C:24]([O:27][CH3:28])[CH:23]=[CH:22][C:18]=1[C:19](O)=[O:20])[CH3:16].OC1C2N=NNC=2C=CC=1>CN(C)C=O.O>[F:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:14])[C:10]([NH:12][NH:13][C:19](=[O:20])[C:18]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[C:25]([CH3:26])[C:17]=2[CH2:15][CH3:16])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 582988572-Ethyl-4-methoxy-3-methylbenzoic acidHCID 698094903,5-DifluorophenylhydroxyacetohydrazideHCID 178418300HCID 178418300、化合物

生成物 1

HCID 69810311N'-(2-(3,5-Difluorophenyl)-2-hydroxyacetyl)-2-ethyl-4-methoxy-3-methylbenzohydrazide収率 65%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6228
Dimethylformamide
溶媒

実験手順

106.0 g of 3,5-difluorophenylhydroxyacetohydrazide (B2) are dissolved in 820 ml of N,N-dimethylformamide. 104.9 g of 2-ethyl-4-methoxy-3-methylbenzoic acid (B1), 153.9 g of N-3-dimethylaminopropyl-N′-ethylcarbodiimide hydrochloride (DAPECI) and 42.8 g of hydroxybenzotriazole (HOBt) are subsequently added. The reaction mixture is cooled in an ice bath during the addition of the compounds enumerated above. The solution is then stirred at room temperature for 24 hours. For work-up, the reaction mixture is diluted with 3.5 litres of water. The resultant suspension is stirred for one hour, subsequently filtered off and washed with additional water. The filter cake is recrystallised from 2.5 litres of methanol, giving 129.0 g of the title compound as colourless solid having a melting point of 197.1° C. (MS: 401 (MNa+)).

後処理

  1. temperatureThe reaction mixture is cooled in an ice bath during the addition of the compounds
  2. filtrationsubsequently filtered off
  3. washwashed with additional water
  4. customThe filter cake is recrystallised from 2.5 litres of methanol

出典と根拠

ORDレコード
ord-2893ba4bf35b47d3ba99463d91e245cc
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08546613B2

反応ノート

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