Methanesulfonyl chloride → 1-[5-(3-Chlorophenyl)-[1,2,4]oxadiazol-3-yl]ethyl methanesulfonate

HRID 732131Notes

Reaction equation

HRID 732131 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:8]=[C:9]([C:13]2[O:17][N:16]=[C:15]([CH:18]([OH:20])[CH3:19])[N:14]=2)[CH:10]=[CH:11][CH:12]=1>C(Cl)Cl>[CH3:1][S:2]([O:20][CH:18]([C:15]1[N:14]=[C:13]([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([Cl:6])[CH:8]=2)[O:17][N:16]=1)[CH3:19])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 578379411-[5-(3-Chlorophenyl)-1,2,4-oxadiazol-3-yl]ethanol

Product 1

HCID 578379891-[5-(3-Chlorophenyl)-[1,2,4]oxadiazol-3-yl]ethyl methanesulfonateYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methane sulfonyl chloride (40 ml, 0.49 mmol) was added to a mixture of TEA (95 ml, 0.67 mmol) and 1-[5-(3-Chloro-phenyl)-1,2,4-oxadiazol-3-yl]-ethanol (100 mg, 0.45 mmol) in DCM (5 ml). After stirring for 15 min the mixture was washed with water and brine, dried and concentrated to yield the title compound (135 mg). 1H NMR: 1.9 (d, 3 H) 3.1 (s, 3 H) 5.9 (q, 1 H) 7.5 (t, 1 H) 7.6 (m, 1 H) 8.0 (m, 1 H) 8.1 (t, 1 H)

Workup

  1. washwas washed with water and brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-488276ce720e4fc7abeb6a7b8a45a92a
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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