Water → HCID 123186264, compound

HRID 711341Notes

Reaction equation

HRID 711341 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH:6]=O.[CH3:17][C:18]([S@:21]([NH2:23])=[O:22])([CH3:20])[CH3:19].O>C(Cl)Cl>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH:6]=[N:23][S@@:21]([C:18]([CH3:20])([CH3:19])[CH3:17])=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 123186264HCID 123186264, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3,5-bis(trifluoromethyl)benzaldehyde (5 g, 20.7 mmol) and (R)-2-methylpropane-2-sulfinamide (3.3 g, 26.9 mmol) in DCM (50 ml) at 0° C., was drop wise added Ti(O-iPr)4 (5.9 g, 24.8 mmol) under N2 atmosphere. After stirring for 20 h at room temperature, the reaction mixture was poured into water (100 mL) with vigorous stirring. The precipitate was filtered off and the filtrate was extracted with DCM (2×100 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous MgSO4, and then concentrated. The residue was purified by silica gel chromatography (PE/EtOAc=5/1 to 2/1) to give the title compound (5.5 g, yield: 78%); m/z (ES+): 346 [M+H]+.

Workup

  1. filtrationThe precipitate was filtered off
  2. extractionthe filtrate was extracted with DCM (2×100 mL)
  3. washThe combined organic layers were washed with brine (100 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (PE/EtOAc=5/1 to 2/1)

Sources & evidence

ORD record
ord-caa00409ed9645ba9105b88cc2b41a18
Source dataset
uspto-grants-2015_11
Patent number
US09181259B2

Reaction notes

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