N,N-Diethylethylenediamine → HCID 57227267, compound

HRID 1608293Notes

Reaction equation

HRID 1608293 reaction equation
[C:1]1([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][N:9]([CH2:18][C:19]([O:21]CC)=O)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:26](CCN)CC)C.C(N(C(C)C)CC)(C)C>CCOCC>[C:1]1([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][N:9]([CH2:18][C:19]([NH2:26])=[O:21])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 60993N,N-DiethylethylenediamineHCID 81531DiisopropylethylamineHCID 14699552HCID 14699552, compound

Product 1

HCID 57227267HCID 57227267, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 10 g (0.033 mol) of ethyl 3,4-diphenyl-1H-pyrazole-1-acetate, 6.9 mL (0.049 mol) of diethylaminoethylamine and 39 mL of diisopropylethylamine was stirred on a steam bath under nitrogen for 18 hours. The reaction was stripped, the residue taken up in about 300 mL of ether and washed twice with water. The ether layer was extracted twice with a total of 150 mL of cold water containing 20 mL of 10% HCl. The combined water extracts were washed once with ether, colled, made basic with solid sodium carbonate, extracted several times with methylene dichloride, dried over sodium sulphate, treated with decolorizing carbon, filtered and stripped. The oily red residue was crystallized from ether to yield 6.86 g of N-[2-diethylamino)ethyl]-3,4-diphenyl-1H-pyrazole-1-acetamide, mp 80°-83° C.

Workup

  1. washwashed twice with water
  2. extractionThe ether layer was extracted twice with a total of 150 mL of cold water containing 20 mL of 10% HCl
  3. washThe combined water extracts were washed once with ether
  4. extractionextracted several times with methylene dichloride
  5. dry with materialdried over sodium sulphate
  6. additiontreated with decolorizing carbon
  7. filtrationfiltered
  8. customThe oily red residue was crystallized from ether

Sources & evidence

ORD record
ord-0a690ac1716048df9dc312bf719514ef
Source dataset
uspto-grants-1989_09
Patent number
US04870095

Reaction notes

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