Water → 4-[(1,3-Dithian-2-ylidene)(phenyl)methyl]-N,N-dimethylaniline

HRID 620063

반응식

HRID 620063 반응식
C[Si](C)(C)[CH:3]1[S:8][CH2:7][CH2:6][CH2:5][S:4]1.C([Li])CCC.[CH3:16][N:17]([CH3:32])[C:18]1[CH:31]=[CH:30][C:21]([C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=O)=[CH:20][CH:19]=1.O>O1CCCC1.CCCCCC.ClCCl>[CH3:32][N:17]([CH3:16])[C:18]1[CH:31]=[CH:30][C:21]([C:22](=[C:3]2[S:8][CH2:7][CH2:6][CH2:5][S:4]2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH:19]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 107374-(Dimethylamino)benzophenoneHCID 834132-Trimethylsilyl-1,3-dithianeHCID 178418339Butyllithium

생성물 1

HCID 133019974-[(1,3-Dithian-2-ylidene)(phenyl)methyl]-N,N-dimethylaniline

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

There is added to a solution of 2-trimethylsilyl-1,3-dithiane (16.2 g) in dry tetrahydrofuran (170 ml) at -65° a 1.9M solution of n-butyllithium in hexane (45 ml). The reaction mixture is progressively warmed to 0° in the course of 31/2 hours and cooled to -65°. A solution of 4-dimethylamino-benzophenone (19.2 g) in dry tetrahydrofuran (100 ml) is than slowly added. The reaction mixture is progressively warmed to room temperature overnight and poured into a mixture of water (1000ml) and dichloromethane (200 ml). After separation of the layers, the aqueous solution is extracted with dichloromethane (3×200 ml). The combined organic solutions was washed with water (100 ml) and dried over magnesium sulphate. The solvents are evaporated in vacuo and the residue is recrystallised from ethyl acetate. The product is dried in vacuo to constant weight to yield (4-dimethylaminophenyl)-(1,3-dithian-2-ylidene)-phenylmethane, m.p. 172°-174°.

후처리

  1. temperaturecooled to -65°
  2. additionthan slowly added
  3. customAfter separation of the layers
  4. extractionthe aqueous solution is extracted with dichloromethane (3×200 ml)
  5. washThe combined organic solutions was washed with water (100 ml)
  6. dry with materialdried over magnesium sulphate
  7. customThe solvents are evaporated in vacuo
  8. customthe residue is recrystallised from ethyl acetate
  9. customThe product is dried in vacuo to constant weight

출처 및 근거

ORD 기록
ord-81be7c86c7d84239b7b61676fc535fd3
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04818765

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