Tert-Butanesulfinamide → HCID 87333909, compound

HRID 1698508Notes

Reaction equation

HRID 1698508 reaction equation
[CH2:1]([S:4]([C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH2:2][CH3:3].[C:15]([S:19]([NH2:21])=[O:20])([CH3:18])([CH3:17])[CH3:16]>[O-]CC.[Ti+5].[O-]CC.[O-]CC.[O-]CC.[O-]CC.C1COCC1>[CH3:16][C:15]([S:19](/[N:21]=[CH:11]/[C:10]1[CH:13]=[CH:14][C:7]([S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5])=[CH:8][CH:9]=1)=[O:20])([CH3:18])[CH3:17]

Participants

5

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 204932624-(Propane-1-sulfonyl)-benzaldehyde

Product 1

HCID 87333909HCID 87333909, compound

Reagents, catalysts & solvents 2

HCID 178468024HCID 178468024, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-(Propylsulphonyl)benzaldehyde (1.81 g, 8.53 mmol, prepared as described in Example 47a, tert-butyl sulphinamide (1.55 g, 12.8 mmol), titanium(V) ethoxide (3.58 mL, 17.1 mmol) and THF (50 mL) were heated at reflux for 3 h then stirred at room temperature overnight. The reaction mixture was quenched with water (200 mL) before addition of ethyl acetate (200 mL). Celite was added and the mixture stirred for 15 min before being filtered. The phases were separated and the organic extract dried (MgSO4) and concentrated. The yield of the title compound was assumed to be quantitative and the material was used without further purification. m/z (ES+) 316 (M+H).

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 3 h
  3. customThe reaction mixture was quenched with water (200 mL) before addition of ethyl acetate (200 mL)
  4. additionCelite was added
  5. stirringthe mixture stirred for 15 min
  6. filtrationbefore being filtered
  7. customThe phases were separated
  8. extractionthe organic extract
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customthe material was used without further purification

Sources & evidence

ORD record
ord-b9026cb387d2437ca7b0c276c5ec3713
Source dataset
uspto-grants-2012_04
Patent number
US08163956B2

Reaction notes

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