Methanesulfonyl chloride → HCID 86695323, compound

HRID 572857Notes

Reaction equation

HRID 572857 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([O:21][CH:22]1[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]1)[C:11]1[CH:12]=[C:13]([S:17][CH2:18][CH2:19][OH:20])[CH:14]=[CH:15][CH:16]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>ClCCl.C(N(CC)CC)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([O:21][CH:22]1[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]1)[C:11]1[CH:12]=[C:13]([S:17][CH2:18][CH2:19][O:20][S:30]([CH3:29])(=[O:32])=[O:31])[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 66836004HCID 66836004, compound

Product 1

HCID 86695323HCID 86695323, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 2-{3-[benzothiazol-2-yl(1-methyl piperidin-4-yloxy)-methyl]phenylsulfanyl}ethanol (400 mg) in dichloromethane (5 mL) is added methanesulfonylchloride (1.25 molar equivalent) in dichloromethane (1.5 mL) and triethylamine (1.5 molar equivalent). The reaction mixture is stirred overnight at room temperature. Volatiles are removed under reduced pressure to dryness. Water is added and the aqueous phase is extracted by diethylether. The organic phase is dried over magnesium sulfate and concentrated. The residue is purified by column chromatography (dichloromethane/methanol from 98/2) to afford methanesulfonic acid 2-{3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenylsulfanyl}ethyl ester that will be used without further purification.

Workup

  1. customVolatiles are removed under reduced pressure to dryness
  2. additionWater is added
  3. extractionthe aqueous phase is extracted by diethylether
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is purified by column chromatography (dichloromethane/methanol from 98/2)

Sources & evidence

ORD record
ord-f5cc5ea9facd4a56bee97478b8c3dc19
Source dataset
uspto-grants-2015_05
Patent number
US09029357B2

Reaction notes

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