N,N-Dimethylethylenediamine → N-[2-(dimethylamino)ethyl]-4,5-diphenyl-1H-pyrazole-1-acetamide hemihydrate

HRID 704823Notes

Reaction equation

HRID 704823 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][N:10]([CH2:18][C:19]([O:21]CC)=[O:20])[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:24][N:25]([CH2:27][CH2:28][NH2:29])[CH3:26]>CCOCC>[OH2:20].[CH3:24][N:25]([CH3:26])[CH2:27][CH2:28][NH:29][C:19](=[O:21])[CH2:18][N:10]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=[N:9]1.[CH3:24][N:25]([CH2:27][CH2:28][NH:29][C:19](=[O:21])[CH2:18][N:10]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=[N:9]1)[CH3:26]

Participants

4

Reactant 2

HCID 66053N,N-Dimethylethylenediamine2×HCID 146995514,5-Diphenyl-1-(ethoxycarbonylmethyl)-pyrazole

Product 1

HCID 67948068N-[2-(dimethylamino)ethyl]-4,5-diphenyl-1H-pyrazole-1-acetamide hemihydrateYield 69.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 9 g (0.029 mol) of ethyl 4,5-diphenyl-1H-pyrazole-1-acetate of Example 1 and 31 mL (0.029 mol) of dimethylaminoethylamine was stirred on a steam bath under nitrogen for 18 hours. The excess dimethylamino ethylamine was stripped in vacuo, the residue dissolved in 300 mL of ether, treated with decolorizing carbon, filtered, and stripped to approximately 10 g of residue. This was triturated in water, filtered, washed and recrystallized from ether to yield 7.16 g of N-[2-(dimethylamino)ethyl]-4,5-diphenyl-1H-pyrazole-1-acetamide hemihydrate, mp 85°-88° C.

Workup

  1. additiontreated with decolorizing carbon
  2. filtrationfiltered
  3. customThis was triturated in water
  4. filtrationfiltered
  5. washwashed
  6. customrecrystallized from ether

Sources & evidence

ORD record
ord-43fcf8fa129140adbfc02805ba354459
Source dataset
uspto-grants-1991_01
Patent number
US04988725

Reaction notes

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