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

HRID 473075Notes

Reaction equation

HRID 473075 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@H:7]([NH:12][S:13]([CH:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])[CH2:6]2.S(Cl)([Cl:21])=O>C(Cl)Cl>[Cl:21][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@H:7]([NH:12][S:13]([CH:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])[CH2:6]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67088215(S)-N-(5-(hydroxymethyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

Product 1

HCID 67088052(S)-N-(5-(chloromethyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-N-(5-(hydroxymethyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide (2.57 mmol, 692 mg) was dissolved in DCM (10 mL), thionyl chloride (5.14 mmol, 0.373 mL, 611 mg) added and the solution stirred at room temperature. After 45 min the mixture was concentrated then azeotroped with dichloromethane (4×10 mL) to give a yellow oil. This was used immediately in step f.

Workup

  1. concentrationAfter 45 min the mixture was concentrated
  2. customthen azeotroped with dichloromethane (4×10 mL)
  3. customto give a yellow oil

Sources & evidence

ORD record
ord-5446f793be0744479d219a70bdf43c5a
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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