Diisopropylamine → HCID 19852683, compound

HRID 1607225Notes

Reaction equation

HRID 1607225 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:11]2[CH2:15][CH2:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[N:12]2)=[O:10])=[CH:4][CH:3]=1.C(NC(C)C)(C)C.C([Li])CCC.Cl[C:36]([O:38][CH2:39][CH3:40])=[O:37]>O1CCCC1.CCCCCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([N:11]2[CH2:15][CH:14]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:13]([C:16]3[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=3)=[N:12]2)=[O:10])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 10928Ethyl chloroformateHCID 1626063-(4-Chlorophenyl)-1-(4-chlorophenylcarbamoyl)-2-pyrazolineHCID 178418339Butyllithium

Product 1

HCID 19852683HCID 19852683, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-20 °C

Procedure

To 3.2 g of N,3-bis-(4-chlorophenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide dissolved in 20 ml of tetrahydrofuran and cooled in an acetone bath maintained at -20° C., was added 1.5 ml of diisopropyl amine and 8.0 ml of a 2.7 molar solution of butyllithium in hexane. The resulting solution was stirred for 20 minutes and then cooled to -70° C. To this solution was added 0.5 ml of ethyl chloroformate. The reaction was allowed to stir for 10 minutes and then allowed to warm to room temperature over 10 minutes. The reaction was quenched with 1.0 ml of acetic acid and 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 3.3 g of N,3-bis-(4-chlorophenyl)-4-carboethoxy-4,5-dihydro-1H-pyrazole-1-carboxamide. NMR and IR data were consistent with the structure.

Workup

  1. temperaturecooled in an acetone bath
  2. temperaturecooled to -70° C
  3. stirringto stir for 10 minutes
  4. temperatureto warm to room temperature over 10 minutes
  5. customThe reaction was quenched with 1.0 ml of acetic acid
  6. customthe reaction mixture was partitioned between diethyl ether and water
  7. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationThe resulting solution was filtered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-946e89a826774fd6aae783e8bda6e8fe
Source dataset
uspto-grants-1989_09
Patent number
US04863947

Reaction notes

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