Benzyl Bromide → N,3-bis-(4-chlorophenyl)-4-benzyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

HRID 978164Notes

Reaction equation

HRID 978164 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([N:23]2[CH2:27][CH:26]([CH3:28])[C:25]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)=[N:24]2)=[O:22])=[CH:16][CH:15]=1.[CH2:36](Br)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>O1CCCC1.CCCCCC.C(O)(=O)C>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([NH:20][C:21]([N:23]2[CH2:27][C:26]([CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([CH3:28])[C:25]([C:29]3[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=3)=[N:24]2)=[O:22])=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 7498Benzyl BromideHCID 7912DiisopropylamineHCID 13752557N,3-bis-(4-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamideHCID 178418339Butyllithium

Product 1

HCID 19852732N,3-bis-(4-chlorophenyl)-4-benzyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To 2.1 g of diisopropylamine dissolved in 15 ml of tetrahydrofuran and cooled in an ice salt bath was added 8.0 ml of a 2.7 molar solution of n-butyllithium in hexane. After stirring for 5 minutes a solution of 3.4 g of N,3-bis-(4-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide (Example G) in 15 ml of tetrahydrofuran was added and the resulting solution stirred for 15 minutes. To this solution was added 1.5 ml of benzyl bromide and, after 5 minutes 1.5 ml of acetic acid was added. The reaction mixture was partitioned between diethyl ether and water and the organic layer was dried over anhydrous magnesium sulfate. The resulting solution was filtered evaporated in vacuo to give 3.90 g of N,3-bis-(4-chlorophenyl)-4-benzyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide, an oil. NMR and IR data were consistent with the structure.

Workup

  1. temperaturecooled in an ice salt bath
  2. additionwas added
  3. customThe reaction mixture was partitioned between diethyl ether and water
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationThe resulting solution was filtered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-4411ef97cb7d4a9490de3a47f704b7ee
Source dataset
uspto-grants-1987_05
Patent number
US04663341

Reaction notes

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