Ammonium Chloride → 2-benzyloxy-N-[1-(3,5-dichlorophenylthio)-3-methyl-2-oxobutyl]-N-methylacetamide

HRID 1416010

反応式

HRID 1416010 の反応式
[CH2:1]([O:8][CH2:9][C:10]([N:12]([CH3:19])[CH2:13][C:14](=[O:18])[CH:15]([CH3:17])[CH3:16])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[Cl:25][C:26]1[CH:27]=[C:28]([S:33]C2C=C(Cl)C=C(Cl)C=2)[CH:29]=[C:30]([Cl:32])[CH:31]=1.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH2:1]([O:8][CH2:9][C:10]([N:12]([CH:13]([S:33][C:28]1[CH:29]=[C:30]([Cl:32])[CH:31]=[C:26]([Cl:25])[CH:27]=1)[C:14](=[O:18])[CH:15]([CH3:17])[CH3:16])[CH3:19])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 211871173,5-DichlorophenylsulfideHCID 221309122-benzyloxy-N-methyl-N-(3-methyl-2-oxobutyl)acetamideHCID 178418339Butyllithium

生成物 1

HCID 221306862-benzyloxy-N-[1-(3,5-dichlorophenylthio)-3-methyl-2-oxobutyl]-N-methylacetamide収率 47%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

In 2 ml of dry tetrahydrofuran was dissolved 100 mg (0.4 mmol )of 2-benzyloxy-N-methyl-N-(3-methyl-2-oxobutyl)acetamide (18a'), and there was added 223 μl (0.4 mmol)of n-butyllithium (1.7 M hexane solution)with stirring at -78° C. over 10 minutes. After stirring at -78° C. for 1 hour, and a tetrahydrofuran solution (1 ml)of 135 mg (0.4 mmol)of 3,5-dichlorophenylsulfide was added thereto over 10 minutes. After 30 minutes, the temperature was raised up to room temperature, a saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate ester. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel chromatography (hexane/ethyl acetate 5:1)to give 79 mg of 2-benzyloxy-N-[1-(3,5-dichlorophenylthio)-3-methyl-2-oxobutyl]-N-methylacetamide (20)(yield 47%).

後処理

  1. stirringAfter stirring at -78° C. for 1 hour
  2. waitover 10 minutes
  3. waitAfter 30 minutes
  4. temperaturethe temperature was raised up to room temperature
  5. extractionthe mixture was extracted with ethyl acetate ester
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by silica gel chromatography (hexane/ethyl acetate 5:1)to

出典と根拠

ORDレコード
ord-eff25180eddf4bb88481975cbe0a97d5
出典データセット
uspto-grants-1999_06
特許番号
US05910506

関連ノート

読み込み中…