1,2-Dimethylhydrazine dihydrochloride → 3-bromo-1-(3-chloro-2-pyridinyl)-N-[2-(N,N'-dimethylhydrazinocarbonyl)-6-methyl-4-nitrophenyl]-1H-pyrazole-5-carboxamide

HRID 2427004Notes

Reaction equation

HRID 2427004 reaction equation
Cl.Cl.[CH3:3][NH:4][NH:5][CH3:6].C(=O)([O-])[O-].[K+].[K+].[Br:13][C:14]1[CH:18]=[C:17]([C:19]2[O:24][C:23](=[O:25])[C:22]3[CH:26]=[C:27]([N+:31]([O-:33])=[O:32])[CH:28]=[C:29]([CH3:30])[C:21]=3[N:20]=2)[N:16]([C:34]2[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][N:35]=2)[N:15]=1>O.CN(C)C=O>[Br:13][C:14]1[CH:18]=[C:17]([C:19]([NH:20][C:21]2[C:29]([CH3:30])=[CH:28][C:27]([N+:31]([O-:33])=[O:32])=[CH:26][C:22]=2[C:23]([N:4]([CH3:3])[NH:5][CH3:6])=[O:25])=[O:24])[N:16]([C:34]2[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][N:35]=2)[N:15]=1

Participants

6

Reactant 3

HCID 93801,2-Dimethylhydrazine dihydrochlorideHCID 11430Potassium CarbonateHCID 668538342-[3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-8-methyl-6-nitro-4H-3,1-benzoxazin-4-one

Product 1

HCID 592868873-bromo-1-(3-chloro-2-pyridinyl)-N-[2-(N,N'-dimethylhydrazinocarbonyl)-6-methyl-4-nitrophenyl]-1H-pyrazole-5-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 0.26 g of N,N′-dimethylhydrazine dihydrochloride, 2 ml of water, 0.5 g of potassium carbonate and 10 ml of N,N-dimethylformamide was added 0.20 g of 2-[3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-8-methyl-6-nitro-4H-3,1-benzoxazine-4-one. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water, and extracted with ethyl acetate three times. The organic layers were combined, washed successively with water and an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 3-bromo-1-(3-chloro-2-pyridinyl)-N-[2-(N,N′-dimethylhydrazinocarbonyl)-6-methyl-4-nitrophenyl]-1H-pyrazole-5-carboxamide of the formula:

Workup

  1. extractionextracted with ethyl acetate three times
  2. washwashed successively with water
  3. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5a375c7e92384104919ce35cc80ff874
Source dataset
uspto-grants-2011_06
Patent number
US07968573B2

Reaction notes

Loading…