Ammonium Chloride → HCID 22762982, compound

HRID 1112771Notes

Reaction equation

HRID 1112771 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=[O:18])[CH2:11][CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[CH:4][CH:3]=1.[CH3:19][Mg]Cl.[Cl-].[NH4+]>O1CCCC1>[OH:18][C:10]([CH3:19])([CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:11][CH2:12][N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 20518975HCID 20518975, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 22762982HCID 22762982, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 5 g. of the above ketone in 150 ml. of dry tetrahydrofuran is treated under nitrogen at -50° C. with excess methyl magnesium chloride (12.5 ml. 33M solution in ether). Stirring is continued for 1 hour. The mixture is then allowed to come to room temperature and stirred for an additional hour. A saturated ammonium chloride solution is added and the mixture is extracted with ether. Any product, which separates out at this point is collected by filtration and washed with water and then with ether. The combined ethereal solutions are then washed with water, dried (MgSO4) and evaporated to yield 1-[3-hydroxy-3-methyl-5-(4-chlorophenyl)n-pentyl]imidazole which may be purified by recrystallization from ethyl acetate or by chromatography on silica gel eluting with 10% methanol in dichloromethane.

Workup

  1. customto come to room temperature
  2. stirringstirred for an additional hour
  3. extractionthe mixture is extracted with ether
  4. filtrationis collected by filtration
  5. washwashed with water
  6. washThe combined ethereal solutions are then washed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-fbc7307ab2ef4f12b33dfa7874facb61
Source dataset
uspto-grants-1978_10
Patent number
US04123542

Reaction notes

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