Water → HCID 10808872、化合物

HRID 865237ノート

反応式

HRID 865237 の反応式
[F:1][C:2]([F:10])([F:9])[C:3]([OH:8])([CH3:7])[C:4](O)=[O:5].S(Cl)(Cl)=O.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:18]([C:29]#[N:30])[CH:17]=1.O>CN(C)C(=O)C>[C:23]1([S:22][C:19]2[CH:20]=[CH:21][C:16]([NH:15][C:4](=[O:5])[C:3]([OH:8])([CH3:7])[C:2]([F:10])([F:9])[F:1])=[CH:17][C:18]=2[C:29]#[N:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

6

反応物 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 1471779HCID 1471779、化合物HCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acid

生成物 1

HCID 10808872HCID 10808872、化合物収率 158.7%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
60 °C

実験手順

To a stirred, cooled (-20° C.) solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (2.16 g 13.7 mmol) in N,N-dimethylacetamide (20 mL) was rapidly added thionyl chloride (1.73 g, 14.5 mmol) and the mixture (a precipitate formed after a few minutes) stirred at -20° C. to -10° C. for 1 hour. (4-Amino-2-cyanophenyl)phenyl sulfide (2.08 g, 9.2 mmol) was then added in one portion and the mixture allowed to stir at room temperature overnight. The solution was poured into 500 mL of water and extracted with two 100 mL portions of ethyl ether. The oil obtained in removal of the ethyl ether was chromatographed on 325 g of silica gel using an ethyl ether (0%, 5%, 10% and 20%) in methylene chloride gradient. The proper fractions were combined, the solvent removed in vacuo and the residue heated overnight at 60° C./0.1 mm to yield 5.35 g (93%) of N-(4-phenylthio-3-cyanophenyl)-3,3,3,-trifluoro-2-hydroxy-2-methylpropanamide, mp 124°-126° C. 1H-NMR (300 MHz, d6 -DMSO): 1.59 (s, 3H, CH3), 7.32-7.47 (m, 6H, aromatic), 7.59 (s, 1H, OH), 8.07 (dd 1H, J=8.8, 2.3 Hz, aromatic), 8.33 (d, 1H, J=2.3 Hz, aromatic), 10.48 (s, 1H, NH). MS (CI, CH4): 367(M+1).

後処理

  1. customthe mixture (a precipitate formed after a few minutes)
  2. stirringto stir at room temperature overnight
  3. extractionextracted with two 100 mL portions of ethyl ether
  4. customThe oil obtained in removal of the ethyl ether
  5. customwas chromatographed on 325 g of silica gel using an ethyl ether (0%, 5%, 10% and 20%) in methylene chloride gradient
  6. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-ed21a93935e44a2295e4415aa4d53eff
出典データセット
uspto-grants-1996_10
特許番号
US05565477

反応ノート

読み込み中…