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

HRID 260391

반응식

HRID 260391 반응식
[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]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 62493Pivaloyl chlorideHCID 178527880HCID 178527880, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cc251a9c6a6a40e1b43e1f5041f504af
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05527805

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