Water → 5-[1-isobutyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]-3,6-dihydro-2H-1,3,4-thiadiazin-2-one

HRID 1517184ノート

反応式

HRID 1517184 の反応式
Cl.Br[CH2:3][C:4]([C:6]1[CH:26]=[CH:25][C:9]2[N:10]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=3)=[N:12][C:8]=2[CH:7]=1)=O.N1C=CC=CC=1.[NH:33]([C:35](=[S:39])[O:36]CC)[NH2:34].O>C(O)C>[CH2:21]([N:10]1[C:9]2[CH:25]=[CH:26][C:6]([C:4]3[CH2:3][S:39][C:35](=[O:36])[NH:33][N:34]=3)=[CH:7][C:8]=2[N:12]=[C:11]1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)[CH:22]([CH3:24])[CH3:23]

参加物

6

反応物 4

HCID 962WaterHCID 1049PyridineHCID 12567113O-Ethyl hydrazinecarbothioateHCID 866472782-bromo-1-[1-isobutyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]ethanone hydrochloride

生成物 1

HCID 595690375-[1-isobutyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]-3,6-dihydro-2H-1,3,4-thiadiazin-2-one

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

To a solution of 24 g (54.8 mM) of 2-bromo-1-[1-isobutyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]ethanone hydrochloride in 500 ml of ethanol are added 6.3 ml (78.4 mM) of pyridine and then 8.2 g (78.4 mM) of O-ethyl hydrazinecarbothioate. The reaction medium is then maintained at 80° C. with stirring for 20 hours. Water is then added and the resulting mixture is extracted with ethyl acetate. The organic phase is washed with water and then dried over anhydrous sodium sulfate and evaporated under vacuum. The residue is purified on a column of silica, using a dichloromethane/methanol mixture (98/2). The residue obtained after evaporation is taken up in diethyl ether to give, after filtration, 10 g of 5-[1-isobutyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]-3,6-dihydro-2H-1,3,4-thiadiazin-2-one in the form of a light-beige solid.

後処理

  1. extractionthe resulting mixture is extracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under vacuum
  5. customThe residue is purified on a column of silica
  6. customThe residue obtained
  7. customafter evaporation
  8. customto give
  9. filtrationafter filtration, 10 g of 5-[1-isobutyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]-3,6-dihydro-2H-1,3,4-thiadiazin-2-one in the form of a light-beige solid

出典と根拠

ORDレコード
ord-66f8c4d56527458cacf56e77140b54b3
出典データセット
uspto-grants-2012_07
特許番号
US08232272B2

反応ノート

読み込み中…