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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
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HRID 1037748 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 582988572-Ethyl-4-methoxy-3-methylbenzoic acidHCID 698094903,5-DifluorophenylhydroxyacetohydrazideHCID 178418300HCID 178418300, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매
HCID 6228
Dimethylformamide
용매

실험 절차

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+)).

후처리

  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

출처 및 근거

ORD 기록
ord-2893ba4bf35b47d3ba99463d91e245cc
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08546613B2

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