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

HRID 473078Notes

Reaction equation

HRID 473078 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][C@H:11]([NH:16][S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])[CH2:10]2.S(Cl)([Cl:32])=O>C(Cl)Cl>[Cl:32][CH2:2][C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][C@H:11]([NH:16][S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])[CH2:10]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 46935616(S)-N-(5-(3-(hydroxymethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

Product 1

HCID 68155989(S)-N-(5-(3-(chloromethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-N-(5-(3-(hydroxymethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide (1.053 mmol, 450 mg) in CH2Cl2 (8 mL) was added Thionyl chloride (2.316 mmol, 0.169 mL, 276 mg) and the whole was stirred for 2 h at RT before the reaction mixture was concentrated under reduced pressure and re-dissovled in DCM. The process was repeated ×4 to drive off the excess thionyl chloride. The material was used immediately in the next reaction.

Workup

  1. concentrationwas concentrated under reduced pressure and re-dissovled in DCM
  2. customThe material was used immediately in the next reaction

Sources & evidence

ORD record
ord-d2811fdb9c6b4742921bd0de41e4d9e9
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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