1-Bromodecane → HCID 54561567, compound

HRID 259278Notes

Reaction equation

HRID 259278 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:19]=[CH:18][C:7]([O:8][CH2:9][CH:10]([OH:17])[CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:6][CH:5]=1.CN(C)P(N(C)C)(N(C)C)=O.Br[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH:10]([O:17][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 81731-BromodecaneHCID 12679Hexamethylphosphoramide2×HCID 24758Sodium hydrideHCID 2916479HCID 2916479, compound

Product 1

HCID 54561567HCID 54561567, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 56% dispersion of sodium hydride in mineral oil (480 mg.) is added under nitrogen to a solution of 2.52 g. of 1-[3'-(4"-chlorophenoxy)-2'-hydroxypropyl]imidazole in 6 ml. dry hexamethylphosphoramide. After stirring for 1 hours at room temperature, the temperature is increased to 45° C. and stirring is continued for 2 hours. The solution is then cooled in an ice bath and 2.5 g. of 1-bromodecane in 1 ml. of hexamethylphosphoramide is added. Thereafter, the solution is stirred for 2 hours at room temperature and then for 16 hours at 50° C. The reaction mixture is poured into water and the resultant aqueous mixture extracted with ether and the ether extracts washed with water. The organic phase is dried over magnesium sulfate and evaporated. The resulting residue is chromatographed on silica gel. Elution with 20% acetone in dichloromethane yields 1-[3'-(4"-chlorophenoxy)-2'-(n-decyloxy)propyl]imidazole.

Workup

  1. temperaturethe temperature is increased to 45° C.
  2. stirringstirring
  3. waitis continued for 2 hours
  4. temperatureThe solution is then cooled in an ice bath
  5. stirringThereafter, the solution is stirred for 2 hours at room temperature
  6. waitfor 16 hours at 50° C
  7. extractionthe resultant aqueous mixture extracted with ether
  8. washthe ether extracts washed with water
  9. dry with materialThe organic phase is dried over magnesium sulfate
  10. customevaporated
  11. customThe resulting residue is chromatographed on silica gel
  12. washElution with 20% acetone in dichloromethane

Sources & evidence

ORD record
ord-05456095977b430093481dbd6ccdc7b1
Source dataset
uspto-grants-1977_07
Patent number
US04036973

Reaction notes

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