1-Chloro-4-(chloromethyl)benzene → Sulconazole

HRID 259593Notes

Reaction equation

HRID 259593 reaction equation
[OH-].[Na+].C(O)(=O)C(O)=O.[Cl:9][C:10]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:11]=1[CH:12]([S:19][C:20]([CH3:22])=O)[CH2:13][N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1.[CH:28]1C(CCl)=[CH:32][CH:31]=[C:30]([Cl:36])[CH:29]=1>CO>[Cl:9][C:10]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:11]=1[CH:12]([S:19][CH2:20][C:22]1[CH:32]=[CH:31][C:30]([Cl:36])=[CH:29][CH:28]=1)[CH2:13][N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14798Sodium HydroxideHCID 21422357HCID 21422357, compound

Product 1

HCID 5318Sulconazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 330 mg sodium hydroxide in 30 ml methanol under nitrogen is added 810 mg of 1-[2,4-dichloro-β-(methylcarbonylthio)phenethyl]imidazole oxalate and the mixture is stirred at room temperature for ca. 30 minutes (until thin layer chromatography shows the disappearance of the ester). α,p-dichlorotoluene (350 mg) is then added, the solution stirred a further 15 minutes and the solvent removed under reduced pressure. Ether and water are then added to the residue and the ether extract washed with water, dried (MgSO4) and concentrated. Dropwise addition of nitric acid (d = 1.42) until precipitation is complete gives the nitrate salt of 1-[2,4-dichloro-β-(4-chlorobenzylthio)phenethyl]imidazole, recrystallized from acetone, mp 130.5°-132° C.

Workup

  1. stirringthe solution stirred a further 15 minutes
  2. customthe solvent removed under reduced pressure
  3. additionEther and water are then added to the residue
  4. extractionthe ether extract
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. additionDropwise addition of nitric acid (d = 1.42)
  9. customuntil precipitation

Sources & evidence

ORD record
ord-7f99420ebc5542cd8eec1a808212ce3f
Source dataset
uspto-grants-1977_07
Patent number
US04038409

Reaction notes

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