Methyl iodide → HCID 13825568, compound

HRID 978163Notes

Reaction equation

HRID 978163 reaction equation
[CH:1](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]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:25]([C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=3)=[N:24]2)=[O:22])=[CH:16][CH:15]=1.IC>O1CCCC1.CCCCCC.C(O)(=O)C>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([N:23]2[CH2:27][C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([CH3:1])[C:25]([C:34]3[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=3)=[N:24]2)=[O:22])=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 173664N,3-Bis(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamideHCID 178418339Butyllithium

Product 1

HCID 13825568HCID 13825568, compoundYield 99%

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 4.2 g of N,3-bis-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamide (Example D) in 15 ml of tetrahydrofuran was added and the resulting solution stirred for 15 minutes. To this solution was added 1.0 ml of iodomethane and, after 15 minutes 1.0 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 4.3 g of N,3-bis-(4-chlorophenyl)-4-phenyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide, melting point 151°-158° C. 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-d3c9a60fb1ed4628afbafd27e93185a6
Source dataset
uspto-grants-1987_05
Patent number
US04663341

Reaction notes

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