Methanesulfonyl chloride → HCID 86703886, compound

HRID 471451Notes

Reaction equation

HRID 471451 reaction equation
[Br:1][C:2]1[C:13]([CH3:14])=[CH:12][C:5]([O:6][CH2:7][CH:8]2[CH2:11][NH:10][CH2:9]2)=[CH:4][C:3]=1[CH3:15].CCN(C(C)C)C(C)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl>[Br:1][C:2]1[C:13]([CH3:14])=[CH:12][C:5]([O:6][CH2:7][CH:8]2[CH2:11][N:10]([S:26]([CH3:25])(=[O:28])=[O:27])[CH2:9]2)=[CH:4][C:3]=1[CH3:15]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86697154HCID 86697154, compound

Product 1

HCID 86703886HCID 86703886, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-(4-Bromo-3,5-dimethyl-phenoxymethyl)-azetidine (400 mg, 1.48 mmol) and DIPEA (0.48 g, 3.7 mmol) are dissolved in 20 mL of dichloromethane and stirred at 0° C. Methanesulfonylchloride (0.12 mL, 1.48 mmol) is added and the reaction mixture is stirred at 0° C. for 2 h. The reaction mixture is washed with water, the organich phase is separated, dried over sodium sulfate and concentrated under vacuum. The crude product is purified by flash chromatography 0-50% ethyl acetate in cyclohexane) to give the title compound (Yield: 330 mg).

Workup

  1. stirringthe reaction mixture is stirred at 0° C. for 2 h
  2. washThe reaction mixture is washed with water
  3. customthe organich phase is separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe crude product is purified by flash chromatography 0-50% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-c1a4a5d9ad174e7183d31fd63fc78435
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

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