Potassium Carbonate → 1-[4-(6-Mercaptohexylthio)-phenyl]-2-methyl-2-morpholine-4-yl-propane-1-one

HRID 376968ノート

反応式

HRID 376968 の反応式
[CH2:1]([SH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][SH:7].C(=O)([O-])[O-].[K+].[K+].Cl[C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:32])[C:23]([CH3:31])([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[CH3:24])=[CH:18][CH:17]=1>CC(N(C)C)=O.C(OCC)(=O)C>[SH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][S:8][C:16]1[CH:17]=[CH:18][C:19]([C:22](=[O:32])[C:23]([CH3:24])([N:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)[CH3:31])=[CH:20][CH:21]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 144911,6-HexanedithiolHCID 157024081-(4-Chlorophenyl)-2-methyl-2-(morpholin-4-yl)propan-1-one

生成物 1

HCID 193606291-[4-(6-Mercaptohexylthio)-phenyl]-2-methyl-2-morpholine-4-yl-propane-1-one

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒2 回

反応条件

温度
85 °C

実験手順

10.0 g (0.066 mol) of 1,6-hexanedithiol are added to a suspension of 3.6 g (0.026 mol) of potassium carbonate in 15 ml of dimethylacetamide. The suspension is heated to 85° C., and a solution of 3.6 g (0.013 mol) of 1-(4-chlorophenyl)-2-methyl-2-morpholin-4-yl-propan-1-one in 20 ml of dimethylacetamide is added dropwise over 20 min. After stirring for 18 h, the reaction mixture is cooled, diluted with ethyl acetate (60 ml), and filtered. The filtrate is washed with water (3×50 ml), dried over MgSO4, and concentrated i.v. (85° C./5 mm Hg). The resulting oil is purified by flash chromatography on silica gel (hexane/ethyl acetate 85:15) to a pale yellow oil which crystallizes to a colorless solid upon standing. m.p. 61-64° C. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm] 1.31 (s, 6H), 1.35 (t, SH), 1.4-1.8 (m, 8H), 2.53 (q, 2H), 2.57 (t, 4H), 3.00 (t, 2H), 3.69 (t, 4H), 7.24 (d, 2H), 8.50 (d, 2H).

後処理

  1. temperaturethe reaction mixture is cooled
  2. filtrationfiltered
  3. washThe filtrate is washed with water (3×50 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated i.v
  6. custom(85° C./5 mm Hg)
  7. customThe resulting oil is purified by flash chromatography on silica gel (hexane/ethyl acetate 85:15) to a pale yellow oil which
  8. customcrystallizes to a colorless solid

出典と根拠

ORDレコード
ord-ceb9e66f9f3042ef9c89b42bdcc16a9c
出典データセット
uspto-grants-2000_02
特許番号
US06022906

反応ノート

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