Benzaldehyde → 2-methyl-N-benzylidene-propane-2-sulfinamide

HRID 1971318노트

반응식

HRID 1971318 반응식
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]([S:13]([NH2:15])=[O:14])([CH3:12])[CH3:11]>C1COCC1.[Cl-].[Na+].O.CCO.CCO.CCO.CCO.[Ti]>[C:2]1([CH:1]=[N:15][S:13]([C:10]([CH3:12])([CH3:11])[CH3:9])=[O:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 2

HCID 240BenzaldehydeHCID 3382465Tert-Butanesulfinamide

생성물 1

HCID 673910032-methyl-N-benzylidene-propane-2-sulfinamide

시약·촉매·용매 3

HCID 2724286Titanium(IV)ethoxide촉매HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

Benzaldehyde (6 mmol, 1 eq), 2-methyl-propane-2-sulfinic acid amide (1 eq) and tetraethyl orthotitanate (3 eq) are dissolved in anhydrous THF under nitrogen (J. Org. Chem. 2003, 68, 9948-9957). The mixture is stirred at room temperature over night. The mixture is poured in brine and stirred vigorously. The resulting suspension is filtered through Celite and the filter cake is extracted with ethyl acetate. The filtrate is transferred to a separatory funnel, where the aqueous layer is separated and extracted 3× with ethyl acetate. The organic layers are combined, washed with brine, dried over Na2SO4 and concentrated in vacuo. Tert.-butane-sulfinic acid 1-phenyl-methylidene amide is obtained as a clear yellowish oil (90% yield); ES-MS (MH+)=210.2; 1H-NMR (DMSO-d6, 400 MHz): δ [ppm] 8.56 (s, 1H), 7.96-7.93 (m, 2H), 7.63-7.53 (m, 3H), 1.19 (s, 9H).

후처리

  1. stirringstirred vigorously
  2. filtrationThe resulting suspension is filtered through Celite
  3. extractionthe filter cake is extracted with ethyl acetate
  4. customThe filtrate is transferred to a separatory funnel
  5. customwhere the aqueous layer is separated
  6. extractionextracted 3× with ethyl acetate
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0c774d129bab4e9da0cb28ebbf9b6ce8
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431602B2

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