3,4-Dichlorobenzyl chloride → HCID 53817886, compound

HRID 259274Notes

Reaction equation

HRID 259274 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][C:19]=1[Cl:20])[O:7][CH2:8][CH:9]([OH:16])[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.Cl[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=1>CN(C)P(N(C)C)(N(C)C)=O>[Cl:30][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=1[Cl:29])[CH2:22][O:16][CH:9]([CH2:8][O:7][C:6]1[CH:17]=[CH:18][C:19]([Cl:20])=[C:4]([Cl:3])[CH:5]=1)[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

5

Reactant 3

HCID 76093,4-Dichlorobenzyl chlorideHCID 24758Sodium hydrideHCID 54187735HCID 54187735, compound

Product 1

HCID 53817886HCID 53817886, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent2×

Conditions

Temperature
25 °C

Procedure

A 56% dispersion of sodium hydride in mineral oil (240 mg.) is added under nitrogen to a solution of 1.43 g. of 1-[3'-(3",4"-dichlorophenoxy)-2'-hydroxypropyl]imidazole in 4 ml. of dry hexamethylphosphoramide. The reaction mixture is then stirred for 1 hour at 25° C., and then 1 hour at 45° C. The solution is then cooled in an ice bath and 1.07 g. of α,3,4-trichlorotoluene in 1 ml. hexamethylphosphoramide is added dropwise with stirring. The reaction mixture is then stirred for 1 hour at 5° C., and then for 1 hour at 25° C., and finally for 2 hours at 45° C. The mixture is then poured into 100 ml. of 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 and eluted with 30% acetone in dichloromethane to yield pure 1-[2'-(3",4"-dichlorobenzyloxy)-3'-(3",4"-dichlorophenoxy)propyl]imidazole which is taken up in ether and treated with nitric acid yielding, after recrystallization of the crude salt from ethyl acetate/ether, 1-[2'-(3",4"-dichlorobenzyloxy)-3'-(3",4"-dichlorophenoxy)propyl]imidazole nitrate, m.p. 116°-118.5° C.

Workup

  1. custom1 hour
  2. customat 45° C
  3. temperatureThe solution is then cooled in an ice bath
  4. stirringwith stirring
  5. stirringThe reaction mixture is then stirred for 1 hour at 5° C.
  6. waitfor 1 hour at 25° C.
  7. waitfinally for 2 hours at 45° C
  8. additionThe mixture is then poured into 100 ml
  9. extractionof water and the resultant aqueous mixture extracted with ether
  10. washthe ether extracts washed with water
  11. dry with materialThe organic phase is dried over magnesium sulfate
  12. customevaporated
  13. customThe resulting residue is chromatographed on silica gel
  14. washeluted with 30% acetone in dichloromethane

Sources & evidence

ORD record
ord-fc8ac49190924151a2112f4367e2c74c
Source dataset
uspto-grants-1977_07
Patent number
US04036970

Reaction notes

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