Dimethyl Sulfoxide → HCID 20435048, compound

HRID 1154350Notes

Reaction equation

HRID 1154350 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:13][CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1.C(N(CC)CC)C>C(Cl)Cl.O>[CH2:14]([N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)[CH2:13][C:12](=[O:11])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 20282535HCID 20282535, compound

Product 1

HCID 20435048HCID 20435048, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

Oxalyl chloride (3.0 ml) in methylene chloride (75 ml) was placed in a flask and cooled to -50° C. to -60° C. Dimethyl sulfoxide (5.1 ml) in 15 ml of methylene chloride was then added followed by 5.88 g of 1-(3-hydroxyoctyl)imidazole dissolved in 30 ml of methylene chloride. The reaction mixture was stirred for 30 minutes at the initial temperature. Triethylamine (21 ml) was added to the reaction mixture which was then allowed to warm to room temperature. Water (100 ml) was added, the organic layer separated and the aqueous layer extracted with methylene chloride (2×50 ml). The organic layers were dried over MgSO4 and the solvent removed to give 1-(octan-3-on-1-yl)imidazole as an oil.

Workup

  1. temperaturecooled to -50° C. to -60° C
  2. customthe organic layer separated
  3. extractionthe aqueous layer extracted with methylene chloride (2×50 ml)
  4. dry with materialThe organic layers were dried over MgSO4
  5. customthe solvent removed

Sources & evidence

ORD record
ord-e6c1444e64a5459e94d34506017ba211
Source dataset
uspto-grants-1984_12
Patent number
US04489087

Reaction notes

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