Potassium Hydroxide → HCID 178505562, compound

HRID 1596300Notes

Reaction equation

HRID 1596300 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9](=[CH:26]N2CCCC2)[CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][C:15](=[CH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[OH-].[K+].[NH2:35][C:36]([NH2:38])=[S:37]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH2:10][CH2:11][N:12]3[CH2:13][CH2:14][C:15](=[CH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[F:25])[CH2:16][CH2:17]3)=[CH:26][N:38]=[C:36]([SH:37])[N:35]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 2723790ThioureaHCID 69949873HCID 69949873, compound

Product 1

HCID 178505562HCID 178505562, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 3.70 g of the crude 1-[4-(4-fluorophenyl)-4-oxo-3-pyrrolidinomethylenebutyl]-4-(2-fluorobenzylidene)piperidine obtained in Example 5 were added a solution of 0.45 g of potassium hydroxide in 40 ml of ethanol and 1.23 g of thiourea, followed by reflux with heating with stirring for 5 hours. The reaction solution was concentrated under reduced pressure, and to the residue were added a saturated aqueous ammonium chloride solution and a little amount of ethyl acetate. The precipitated crystals were collected by filtration, and recrystallized from ethyl acetate to give 1.27 g of 4-(4-fluorophenyl)-5-[2-[4-(2-fluorobenzylidene)piperidin-1-yl]ethyl]-2-mercaptopyrimidine.

Workup

  1. temperatureby reflux
  2. temperaturewith heating
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionto the residue were added a saturated aqueous ammonium chloride solution
  5. filtrationThe precipitated crystals were collected by filtration
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6d2698ec6d144e8887886a85ef9dd4db
Source dataset
uspto-grants-2001_09
Patent number
US06291467B1

Reaction notes

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