HCID 58298857, compound → N'-(2-(3,5-Difluorophenyl)-2-hydroxyacetyl)-2-ethyl-4-methoxy-3-methylbenzohydrazide

HRID 1037748Notes

Reaction equation

HRID 1037748 reaction equation
[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

Participants

6

Reactant 3

HCID 58298857HCID 58298857, compoundHCID 698094903,5-DifluorophenylhydroxyacetohydrazideHCID 178418300HCID 178418300, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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+)).

Workup

  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

Sources & evidence

ORD record
ord-2893ba4bf35b47d3ba99463d91e245cc
Source dataset
uspto-grants-2013_10
Patent number
US08546613B2

Reaction notes

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