Water → HCID 22184195、化合物

HRID 612348

反応式

HRID 612348 の反応式
[OH:1][N:2]=[C:3]1[CH:8]=[CH:7][C:6](=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]#[N:11])[CH:5]=[CH:4]1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27].O>O1CCCC1>[CH3:25][S:26]([O:1][N:2]=[C:3]1[CH:8]=[CH:7][C:6](=[C:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:10]#[N:11])[CH:5]=[CH:4]1)(=[O:28])=[O:27]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 3468332-(4-(Hydroxyimino)cyclohexa-2,5-dien-1-ylidene)-2-phenylacetonitrile

生成物 1

HCID 22184195HCID 22184195、化合物収率 70%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

10 g (45 mmol) of (4-Hydroxyimino-cyclohexa-2,5-dienylidene)-phenyl-acetonitrile are dissolved in 100 ml of tetrahydrofuran (THF) and cooled in an ice bath. After adding 9.41 ml (68 mmol) of triethylamine to the solution, 3.83 ml (50 mmol) of methanesulfonyl chloride are added dropwise, keeping the temperature below 5° C. The reaction mixture is gradually warmed to room temperature, and stirred for 1 hr. The reaction mixture is poured into 200 ml of water, and extracted with ethyl acetate. The organic phase is washed with hydrochloric acid solution, water, and sodium chloride solution. The organic phase is dried over MgSO4, the solvent is distilled off, and the residue is purified by recrystallization from toluene. 9.4 g (70%) of (4-Methylsulfonyloxyimino-cyclohexa-2,5-dienylidene)-phenyl-acetonitrile are obtained in the form of a yellow-green crystal having a melting point of 137-139° C. (dec.). 1H-NMR shows that the product is a 82:18 mixture of the E and Z isomers (two dxd signals for H-C(2 or 6) at 6.78 and 6.91 ppm.

後処理

  1. temperaturecooled in an ice bath
  2. additionare added dropwise
  3. customthe temperature below 5° C
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed with hydrochloric acid solution, water, and sodium chloride solution
  6. dry with materialThe organic phase is dried over MgSO4
  7. distillationthe solvent is distilled off
  8. customthe residue is purified by recrystallization from toluene

出典と根拠

ORDレコード
ord-d3822b41411a457ca102026d4824804d
出典データセット
uspto-grants-1999_12
特許番号
US06004724

関連ノート

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