Dimethylformamide → HCID 178516667、化合物

HRID 962388ノート

反応式

HRID 962388 の反応式
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

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 6348Carbon DisulfideHCID 24758Sodium hydride2 回HCID 5194142'-Fluoro-6'-(trifluoromethyl)acetophenone

生成物 1

HCID 178516667HCID 178516667、化合物

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 241Benzene溶媒HCID 962Water溶媒

反応条件

温度
125 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8a2359b1f3a94e8aa1626c7bfdc5bb50
出典データセット
uspto-grants-1998_06
特許番号
US05759959

反応ノート

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