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

HRID 2102296Notes

Reaction equation

HRID 2102296 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 methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methane sulfonyl chloride (40 μl, 0.49 mmol) was added to a mixture of TEA (95 μl, 0.67 mmol) and 1-[5-(3-chlorophenyl)-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 and the title compound was obtained in 135 mg yield. 1H NMR: 1.9 (d, 3H), 3.1 (s, 3H), 5.9 (q, 1H), 7.5 (t, 1H), 7.6 (m, 1H), 8.0 (m, 1H), 8.1 (t, 1H)

Workup

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

Sources & evidence

ORD record
ord-87b1adcaa6a84d23beecea37949dd1db
Source dataset
uspto-grants-2009_08
Patent number
US07576077B2

Reaction notes

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