N-methyl-2-pyrrolidone → HCID 66853980, compound

HRID 251930Notes

Reaction equation

HRID 251930 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:26])[C:5]2[N:10]=[C:9]([C:11]3[C:12]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[Cl:23])=[N:13][N:14]([CH3:16])[CH:15]=3)[O:8][C:7](=O)[C:6]=2[CH:25]=1.[OH2:27].[NH2:28][NH2:29].CN1CCCC1=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:26])[C:5]([NH:10][C:9]([C:11]2[C:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])=[N:13][N:14]([CH3:16])[CH:15]=2)=[O:8])=[C:6]([C:7]([NH:28][NH2:29])=[O:27])[CH:25]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 24654Hydrazine hydrate (1:1)HCID 66853774HCID 66853774, compound

Product 1

HCID 66853980HCID 66853980, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After 0.19 g of 6-chloro -2-[3 -(2-chlorophenyl)-1-methyl-1H-pyrazol-4-yl]-8-methyl-4H-3,1-benzoxazine-4-one, 0.10 g of hydrazine monohydrate and 10 ml of N-methylpyrrolidinone were mixed under ice-cooling, the mixture was stirred at room temperature for 8 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 0.18 g of N-[4-chloro-2-(hydrazinocarbonyl)-6-methylphenyl]-3-(2-chlorophenyl)-1-methyl-1H-pyrazole-4-carboxamide of the formula:

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a2d5d3132f3e4ea48bbc7c9bf2ba0718
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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