Water → 2,2-Dimethyl-1-(2-thioxothiazolidin-3-yl)propan-1-one

HRID 260391

反応式

HRID 260391 の反応式
[H-].[Na+].[SH:3][C:4]1[S:5][CH2:6][CH2:7][N:8]=1.[CH3:9][C:10]([CH3:15])([CH3:14])[C:11](Cl)=[O:12].O>C1COCC1>[CH3:9][C:10]([CH3:15])([CH3:14])[C:11]([N:8]1[CH2:7][CH2:6][S:5][C:4]1=[S:3])=[O:12]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 62493Pivaloyl chlorideHCID 178527880HCID 178527880、化合物

生成物 1

HCID 117695952,2-Dimethyl-1-(2-thioxothiazolidin-3-yl)propan-1-one収率 91.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a suspension of NaH (60 percent, 1.06 g, 26.5 mmol) in dry THF (10 mL) cooled at zero degrees C was added a solution of 2-mercaptothiazoline (3.0 g, 25.17 mmol) in dry THF (20 mL) followed by stirring at zero degrees C for 10 minutes. To the mixture was added trimethylacetyl chloride (3.1 mL, 25.17 mmol), the resultant mixture was then stirred at 25° C. for two hours. Water was added to the reaction mixture followed by extraction with ethyl acetate (100 mL), dry over anhydrous Na2SO4, and removal of the solvent in vacuo to give a crude product. Flash column chromatography of the crude product (silica gel, 17 percent ethyl ether in petroleum ether) afforded Compound 226 (4.68 g, 91 percent): pale-yellow solid; mp 48°-50° C.; Rf =0.19 (silica, 17 percent ethyl ether in petroleum ether); IR (CHCl3) νmax 2980, 1808, 1738, 1480, 1463, 1396, 1388, 1286, 1251, 1139, 1044, 1003, 874 cm-1 ; 1H NMR (300 MHz, CDCl3) δ 4.21 (t, J=7.3 Hz, 2 H, NCH2CH2S), 3.51 (t, J=7.3 Hz, 2 H, NCH2CH2S), 1.41 (s, 9 H, C(CH3)3); MS (FAB+) m/e (rel intensity) 204 (M+H, 100), 120 (27); HRMS for C8H14NOS2 (M+H), calcd 204.0517, found 204.0500.

後処理

  1. extractionfollowed by extraction with ethyl acetate (100 mL)
  2. dry with materialdry over anhydrous Na2SO4, and removal of the solvent in vacuo
  3. customto give a crude product

出典と根拠

ORDレコード
ord-cc251a9c6a6a40e1b43e1f5041f504af
出典データセット
uspto-grants-1996_06
特許番号
US05527805

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