Thionyl Chloride → N-(5-(chloromethyl)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide

HRID 473087Notes

Reaction equation

HRID 473087 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH:12]([NH:16][S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])[CH2:11][CH2:10]2>C(Cl)Cl>[Cl:3][CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH:12]([NH:16][S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])[CH2:11][CH2:10]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67088175N-(5-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide

Product 1

HCID 67088048N-(5-(chloromethyl)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamideYield 51.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.355 mL, 4.90 mmol) was added to a solution of N-(5-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide (660 mg, 2.450 mmol) in DCM (10 mL). The whole was stirred for 1 h before the reaction mixture was evaporated to dryness and the crude material was purified by silica flash column chromatography (EtOAc/heptane: from 0% to 60% of EtOAc) to afford the title compound as a white solid (360 mg, 51%). MS (ESI): m/z [M−H]− 286.0

Workup

  1. customwas evaporated to dryness
  2. customthe crude material was purified by silica flash column chromatography (EtOAc/heptane: from 0% to 60% of EtOAc)

Sources & evidence

ORD record
ord-03bf058cd915408e85cfa26911a2b999
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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