Dimethyl Sulfoxide → HCID 58356054, compound

HRID 2047466Notes

Reaction equation

HRID 2047466 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]([F:35])([F:34])[C:13]1[CH:14]=[C:15]([N:23]([CH2:31][CH2:32][OH:33])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1.C(N(CC)CC)C>C1COCC1.O>[F:11][C:12]([F:34])([F:35])[C:13]1[CH:14]=[C:15]([N:23]([CH2:31][CH:32]=[O:33])[C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH:16]=[C:17]([C:19]([F:21])([F:20])[F:22])[CH:18]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86655665HCID 86655665, compound

Product 1

HCID 58356054HCID 58356054, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of oxalyl chloride (0.15 mL) in THF (5.0 mL) was cooled to −78° C., DMSO (0.17 mL) in THF (2.0 mL) was slowly added dropwise. The reaction mixture was stirred for 5 min, a solution of the compound (0.34 g) obtained in step 4 in THF (3.0 mL) was added dropwise. The reaction mixture was stirred at −78° C. to −20° C. for 1 hr, and triethylamine (0.88 mL) was added. The reaction mixture was stirred at room temperature for 30 min, poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous ammonium chloride solution and saturated brine, dried and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (solvent gradient; 3→20% ethyl acetate/hexane) to give the title compound (0.23 g, 69%) as a colorless oil.

Workup

  1. stirringThe reaction mixture was stirred at −78° C. to −20° C. for 1 hr
  2. stirringThe reaction mixture was stirred at room temperature for 30 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous ammonium chloride solution and saturated brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was separated
  8. custompurified by silica gel column chromatography (solvent gradient; 3→20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-419624655fcc4698bf9e2dfb6d39cd55
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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