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

HRID 1708997

反応式

HRID 1708997 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

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 (1000 ml ) and dichloromethane (200 ml). After separation of the layers, the aqueous solution is extracted with dichloromethane (3×200 ml). The combined organic solutions are 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°.

後処理

  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 are 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

出典と根拠

ORDレコード
ord-46024b1f7ed94f84adbec3203a3b2645
出典データセット
uspto-grants-1990_08
特許番号
US04946861

関連ノート

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