Dichloromethane → HCID 86666712, compound

HRID 2401337Notes

Reaction equation

HRID 2401337 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2[C:17]([CH3:23])=[N:18][O:19][C:20]=2[CH2:21][OH:22])=[O:9])=[CH:4][CH:3]=1.C(Cl)Cl.CCN(CC)CC.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>O>[CH3:34][S:35]([O:22][CH2:21][C:20]1[O:19][N:18]=[C:17]([CH3:23])[C:16]=1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:8](=[O:9])[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:37])=[O:36]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67811908HCID 67811908, compound

Product 1

HCID 86666712HCID 86666712, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a round bottomed flask was added crude (4-chlorophenyl)(2-(5-(hydroxymethyl)-3-methylisoxazol-4-yl)phenyl)methanone (24.9 mg, 0.076 mmol), DCM (2 mL), and Et3N (21.18 μl, 0.152 mmol). This solution was cooled to 0° C. before addition of MsCl (7.10 μl, 0.091 mmol) and the reaction stirred at 0° C. for 30 min before diluting with water and extracting with DCM. The combined organics were dried over Na2SO4, filtered, and concentrated to afford crude (4-(2-(4-chlorobenzoyl)phenyl)-3-methylisoxazol-5-yl)methyl methanesulfonate.

Workup

  1. extractionextracting with DCM
  2. dry with materialThe combined organics were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ce1fc5c4370b4a4a9d95b14dd181c558
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

Loading…