Hydrazine hydrate (1:1) → HCID 58243744, compound

HRID 389136Notes

Reaction equation

HRID 389136 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]([CH3:30])([C:14]2[N:18]([CH3:19])[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:28])[F:27])=[N:16][N:15]=2)[CH3:13])=[C:6]([CH:10]=1)[C:7](O)=[O:8].C1C=CC2N(O)[N:38]=[N:37]C=2C=1.O.NN>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]([CH3:13])([C:14]2[N:18]([CH3:19])[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:27])[F:28])=[N:16][N:15]=2)[CH3:30])=[C:6]([CH:10]=1)[C:7]([NH:37][NH2:38])=[O:8]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 757711-HydroxybenzotriazoleHCID 58244031HCID 58244031, compound

Product 1

HCID 58243744HCID 58243744, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

5-chloro-2-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl}ethoxy)benzoic acid (1.00 g) was suspended in acetonitrile (10 ml), and WSC•monohydrochloride (654 mg) and HOBt (461 mg) were added to thereto, followed by stirring at room temperature for 30 minutes. A mixture of hydrazine monohydrate (1.1 ml) and acetonitrile (10 ml) was ice-cooled and the above reaction solution was added thereto, followed by stirring for 2 hours. The reaction solution was concentrated under reduced pressure and water and saturated aqueous sodium bicarbonate solution were added thereto, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (chloroform:methanol=100:1 to 99:5). The resulting solid was washed with diisopropylether to obtain, as a white solid, 5-chloro-2-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)benzohydrazide (817 mg).

Workup

  1. temperaturecooled
  2. additionthe above reaction solution was added
  3. stirringby stirring for 2 hours
  4. concentrationThe reaction solution was concentrated under reduced pressure and water and saturated aqueous sodium bicarbonate solution
  5. additionwere added
  6. extractionfollowed by extraction with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel chromatography (chloroform:methanol=100:1 to 99:5)
  10. washThe resulting solid was washed with diisopropylether

Sources & evidence

ORD record
ord-47e0063363e14390b0c3f2c8123da0f2
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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