Diethyl Ether → HCID 66958832, compound

HRID 1360437Notes

Reaction equation

HRID 1360437 reaction equation
O=[C:2]([CH2:8][C:9](=O)[CH2:10][CH2:11][N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Na].C(O)(=O)C(O)=O.[CH2:31]([NH:33][NH2:34])[CH3:32].C(OCC)C>C(O)(=O)C>[CH2:31]([N:33]1[C:9]([CH2:10][CH2:11][N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])=[CH:8][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N:34]1)[CH3:32]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 96181Hydrazine, ethyl-, ethanedioate (1:1)HCID 5360545SodiumHCID 66958840HCID 66958840, compound

Product 1

HCID 66958832HCID 66958832, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A modification of the method described in Part A of Example 11 was followed. A solution of ethyl 2,4-dioxo-6-phthalimidohexanoate, sodium salt (37.64 g, 0.110 mol) in glacial acetic acid (160 L) was cooled to 10° C. before the addition of ethylhydrazine oxalate (16.52 g, 0.110 mol). During the addition, the reaction temperature was maintained between 9 and 11° C. The reaction was complete in two hours. The crude product, a reddish-orange oil, was treated with diethyl ether (150 mL) to form a solid, which was isolated by filtration to provide 26.5 g of ethyl 1-ethyl-5-(2-phthalimidoethyl)-1H-pyrazole-3-carboxylate as a tan solid.

Workup

  1. additionDuring the addition
  2. temperaturethe reaction temperature was maintained between 9 and 11° C
  3. customto form a solid
  4. customwhich was isolated by filtration

Sources & evidence

ORD record
ord-1023664235cb4040838288a1b733b488
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

Loading…