Dimethyl Sulfoxide → HCID 86666720, compound

HRID 2401358Notes

Reaction equation

HRID 2401358 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]2[C:27]([CH3:33])=[N:28][O:29][C:30]=2[CH2:31][OH:32])=[O:19])=[CH:14][CH:13]=1.CCN(CC)CC>C(Cl)Cl.O>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]2[C:27]([CH3:33])=[N:28][O:29][C:30]=2[CH:31]=[O:32])=[O:19])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67811908HCID 67811908, compound

Product 1

HCID 86666720HCID 86666720, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a round bottomed flask was added CH2Cl2 (15 mL) and oxalyl chloride (0.24 mL, 2.75 mmol). The solution was cooled to −78° C. before addition of DMSO (0.29 mL, 4.13 mmol) and the reaction stirred at −78° C. for 15 minutes before addition of (4-chlorophenyl)(2-(5-(hydroxymethyl)-3-methylisoxazol-4-yl)phenyl)methanone (0.451 mg, 1.38 mmol) dissolved in CH2Cl2 (5 mL). The reaction was stirred an additional 15 min at −78° C. before addition of Et3N (0.959 mL, 6.88 mmol) and removal of the cold bath. After warming to room temperature water was added and the layers separated. The aqueous was extracted with CH2Cl2 and the combined organics were dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford 4-(2-(4-chlorobenzoyl)phenyl)-3-methylisoxazole-5-carbaldehyde (0.448 g, 1.38 mmol). LC/MS m/z 326 [M+H]+.

Workup

  1. additionwas added
  2. customthe layers separated
  3. extractionThe aqueous was extracted with CH2Cl2
  4. dry with materialthe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified via Biotage (EtOAc/hex)

Sources & evidence

ORD record
ord-62ad9380f6574e318b439d0ca47c8aaf
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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