Dimethyl Sulfoxide → HCID 86585467, compound

HRID 2304986Notes

Reaction equation

HRID 2304986 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]1[O:13][CH2:14][C:15]([CH2:33][OH:34])([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:21][CH:20]=2)[N:16]=1>C(Cl)Cl>[CH3:11][C:12]1[O:13][CH2:14][C:15]([CH:33]=[O:34])([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:21][CH:20]=2)[N:16]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 71316181{2-Methyl-4-[2-(4-octylphenyl)ethyl]-4,5-dihydro-1,3-oxazol-4-yl}methanol

Product 1

HCID 86585467HCID 86585467, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.059 mL (0.8 mmol) of oxalyl chloride in 1.5 mL of CH2Cl2 at −78° C. was treated with 0.12 mL (1.6 mmol) of DMSO. The resulting mixture was stirred cold for 10 min, 118 mg of (+/−)-2-methyl-4-hydroxymethyl-4-(2-(4-octylphenyl)ethyl)oxazoline (from EXAMPLE 2, Step A) was added and resulting mixture was stirred cold for 30 min. TEA (0.28 mL, 2.0 mmol) was added and the resulting mixture was warmed to rt. The mixture was partitioned between 30 mL of ether and 10 mL of water. The organic layer was separated, dried and concentrated to afford 118 mg (100%) of the title compound.

Workup

  1. customresulting mixture
  2. stirringwas stirred cold for 30 min
  3. customThe mixture was partitioned between 30 mL of ether and 10 mL of water
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-51028a804cbb455fb72c41151c58770b
Source dataset
uspto-grants-2002_08
Patent number
US06437165B1

Reaction notes

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