Pyridine → HCID 67600187, compound

HRID 1417331Notes

Reaction equation

HRID 1417331 reaction equation
[N:1]1([C:6]2[CH:17]=[CH:16][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][NH2:15])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.N1C=CC=CC=1.[CH3:24][O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1>ClCCl>[CH3:24][O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:15][CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:9]2[CH:16]=[CH:17][C:6]([N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)=[CH:7][CH:8]=2)=[O:31])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7477p-Anisoyl chlorideHCID 10922371HCID 10922371, compound

Product 1

HCID 67600187HCID 67600187, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of 2.3 g of 4-[4-(1H-imidazol-1-yl)phenoxy]butaneamine (Example 2) in 50 ml of dichloromethane containing 2 ml of pyridine is treated with 2.0 g of 4-methoxybenzoyl chloride. The reaction mixture is allowed to stand at room temperature for 18 hours, and is then heated at reflux for one hour. The volatiles are removed in vacuo. The residue is partitioned between 100 ml of dichloromethane and 100 ml of water. The dichloromethane layer is dried over Na2SO4, and then heated to gentle boiling. Hexane is then added to turbidity and the mixture cooled at -10° C. A tacky precipitate results and crystals develop in the supernatant solvent. These are collected, washed with hexane, and dried in vacuo at room temperature; m.p. 125°-126° C.; yield, 0.4 g.

Workup

  1. temperatureis then heated
  2. temperatureat reflux for one hour
  3. customThe volatiles are removed in vacuo
  4. customThe residue is partitioned between 100 ml of dichloromethane and 100 ml of water
  5. dry with materialThe dichloromethane layer is dried over Na2SO4
  6. temperatureheated to gentle boiling
  7. additionHexane is then added to turbidity
  8. customA tacky precipitate results
  9. customThese are collected
  10. washwashed with hexane
  11. customdried in vacuo at room temperature
  12. customyield

Sources & evidence

ORD record
ord-9b4a9f8b3f7443d8a06676047733f240
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

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