Water → HCID 58243915, compound

HRID 389135Notes

Reaction equation

HRID 389135 reaction equation
C1C=CC2N(O)N=NC=2C=1.[CH:11]([NH:13][NH2:14])=[O:12].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([O:25][C:26]([CH3:44])([C:28]2[N:32]([CH3:33])[C:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:40]([F:43])([F:42])[F:41])=[N:30][N:29]=2)[CH3:27])=[C:20]([CH:24]=1)[C:21]([OH:23])=O.O>CN(C=O)C>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([O:25][C:26]([CH3:27])([C:28]2[N:32]([CH3:33])[C:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:40]([F:41])([F:43])[F:42])=[N:30][N:29]=2)[CH3:44])=[C:20]([CH:24]=1)[C:21]([NH:14][NH:13][CH:11]=[O:12])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 12229HydrazinecarboxaldehydeHCID 757711-HydroxybenzotriazoleHCID 58244031HCID 58244031, compound

Product 1

HCID 58243915HCID 58243915, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

WSC•monohydrochloride (130 mg), HOBt (110 mg) and formic hydrazide (60 mg) were sequentially added to a solution of 5-chloro-2-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)benzoic acid (300 mg) in DMF (6 ml), followed by stirring at room temperature for 4 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was sequentially washed with saturated aqueous sodium bicarbonate solution, water and then saturated brine in this order, and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure to obtain 5-chloro-N′-formyl-2-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)benzohydrazide (230 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was sequentially washed with saturated aqueous sodium bicarbonate solution, water
  3. dry with materialsaturated brine in this order, and dried over anhydrous magnesium sulfate
  4. customthe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-e4fb30b832a9414b8f53fec11d9c7260
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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