Methyl iodide → HCID 13825583, compound

HRID 1607219Notes

Reaction equation

HRID 1607219 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([N:13]2[CH2:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([CH3:18])[C:15]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)=[N:14]2)=[O:12])=[CH:6][CH:5]=1.[H][H].I[CH3:35]>>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH3:35])[C:11]([N:13]2[CH2:17][C:16]([CH3:18])([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:15]([C:25]3[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=3)=[N:14]2)=[O:12])=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13825568HCID 13825568, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13825583HCID 13825583, compound

Procedure

To a 100 ml round bottomed flask was added 0.40 g (0.01 mole) of 60% sodium hydride. The sodium hydride was washed twice with hexane and 10 ml of dimethylformamide was added. Then, 2.1 g (0.05 mole) N,3-bis-(4-chlorophenyl)-4-methyl-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamide (Example 2) was added portionwise. After hydrogen evolution ceased 1 ml of iodomethane was added and the mixture was stirred for 1 hour. The reaction mixture was partitioned between ether and water and the organic layer dried, filtered, concentrated, and chromatographed yielding 1.5 g of N,3-bis-(4-chlorophenyl)-N,4-dimethyl-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamide, mp 132°-135° C. NMR and IR data were consistent with the structure.

Workup

  1. washThe sodium hydride was washed twice with hexane and 10 ml of dimethylformamide
  2. additionwas added
  3. additionwas added
  4. customThe reaction mixture was partitioned between ether and water
  5. customthe organic layer dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed

Sources & evidence

ORD record
ord-43c36e782e764a899e4bbd49dd2baf44
Source dataset
uspto-grants-1989_09
Patent number
US04863947

Reaction notes

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