Dimethylamine → Ethanamine, 2-[[4-[3-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]phenyl]sulfonyl]-N,N-dimethyl-

HRID 1032871Notes

Reaction equation

HRID 1032871 reaction equation
[CH:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:16][CH2:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)=[N:13]2)=[CH:8][CH:7]=1)(=[O:5])=[O:4])=[CH2:2].[CH3:24][NH:25][CH3:26]>C(O)C.C(O)(=O)C>[CH3:24][N:25]([CH2:2][CH2:1][S:3]([C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH2:16][CH2:15][C:14]([C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)=[N:13]2)=[CH:10][CH:11]=1)(=[O:4])=[O:5])[CH3:26]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 834053-(4-Chlorophenyl)-4,5-dihydro-1-(4-(vinylsulphonyl)phenyl)-1H-pyrazole

Product 1

HCID 82580Ethanamine, 2-[[4-[3-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]phenyl]sulfonyl]-N,N-dimethyl-

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent2×

Procedure

6.9 g of 1-(p-vinylsulfonylphenyl)-3-(p-chlorophenyl)-2-pyrazoline are stirred in 5.5 g of a 33% solution of dimethylamine in ethanol and 15 ml of ethanol. The solution is heated gradually over one hour to 78° C. and stirring is continued until the starting material is dissolved and a concentrated sample is soluble in dilute acetic acid. The solution is allowed to cool to room temperature, whereupon a dense precipitate of the reaction product forms. This precipitate is collected by suction filtration, washed with ethanol and dried, affording 6.7 g of 1-(p-dimethylaminoethylsulfonylphenyl)-3-(p-chlorophenyl)-2-pyrazoline (formula 103). 1-(p-Diethylaminoethylsulfonylphenyl)-3-(p-chlorophenyl)-2-pyrazoline (m.p. 104°-107° C.) is obtained in analogous manner using diethylamine in isopropanol instead of dimethylamine in ethanol.

Workup

  1. temperatureThe solution is heated gradually over one hour to 78° C.
  2. dissolutionis dissolved
  3. filtrationThis precipitate is collected by suction filtration
  4. washwashed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-b23ac0bc2105499d9a625ce97ebc1664
Source dataset
uspto-grants-1994_05
Patent number
US05308545

Reaction notes

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