Pyridine → HCID 178468484, compound

HRID 1605020Notes

Reaction equation

HRID 1605020 reaction equation
[C:1]([C:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=1[C:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[NH:12][N:11]=1)([OH:3])=[O:2].N1C=CC=[CH:23][CH:22]=1.S(Cl)(Cl)=O>C(O)C>[C:1]([C:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=1[C:10]1[CH:14]=[C:13]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:12][N:11]=1)([O:3][CH2:22][CH3:23])=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 178524023HCID 178524023, compound

Product 1

HCID 178468484HCID 178468484, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(2-carboxy-1-cyclohexen-1-yl)-5-phenylpyrazole (15.0 g) and pyridine (125 ml) is treated at 25°C with thionyl chloride (13.5 g); after stirring for 2 hours, ethanol (40.0 g) is added, and the mixture is stirred for 3 hours. The reaction mixture is partitioned between water and methylene chloride; the organic layer is washed with water and evaporated to give 3-(2-carboethoxy-1-cyclohexen-1-yl)-5-phenylpyrazole.

Workup

  1. stirringthe mixture is stirred for 3 hours
  2. customThe reaction mixture is partitioned between water and methylene chloride
  3. washthe organic layer is washed with water
  4. customevaporated

Sources & evidence

ORD record
ord-49bcedd51bf947e692528ba64bed7a5c
Source dataset
uspto-grants-1976_04
Patent number
US03948937

Reaction notes

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