Dimethylformamide → HCID 178516667, 화합물

HRID 962388노트

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HRID 962388 반응식
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[C:12](=[O:14])[CH3:13].[C:15](=[S:17])=[S:16].CN(C)C=O.[H-].[Na+]>C1C=CC=CC=1.O.C(O)(=O)C>[OH:14][C:12]1[C:3]2[C:2](=[CH:7][CH:6]=[CH:5][C:4]=2[C:8]([F:11])([F:10])[F:9])[S:17][C:15](=[S:16])[CH:13]=1

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 6348Carbon DisulfideHCID 24758Sodium hydride2회HCID 5194142'-Fluoro-6'-(trifluoromethyl)acetophenone

생성물 1

HCID 178516667HCID 178516667, 화합물

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 241Benzene용매HCID 962Water용매

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온도
125 °C

실험 절차

A mixture of 2'-fluoro-6'-(trifluoromethyl)acetophenone (3.0 g, 14.5 mmol), carbon disulfide (1.5 mL, 26.7 mmol) and dimethylformamide (DMF) (12.5 mL) in benzene at 15°-25° C. is treated portion-wise with a 60% dispersion of sodium hydride in mineral oil (1.15 g, 28.8 mmol NaH) over a 1.5 hour period, stirred for 0.5 hour, heated at 125° C. for 1 hour, cooled to room temperature and diluted with water. The resultant mixture is treated with acetic acid and extracted with ether. The aqueous phase is acidified to pH 3 with HCl and extracted with ethyl acetate. The ethyl acetate extracts are combined, washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo to give an orange oil residue. The residue is crystallized from diethyl ether/hexanes to give the title product as a white solid, 3.0 g (79% y), mp 142°-144° C., identified by IR, 1HNMR, 19FNMR and mass spectral analyses.

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted with ether
  3. extractionextracted with ethyl acetate
  4. washwashed sequentially with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give an orange oil residue
  8. customThe residue is crystallized from diethyl ether/hexanes

출처 및 근거

ORD 기록
ord-8a2359b1f3a94e8aa1626c7bfdc5bb50
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05759959

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