Ammonium formate → HCID 86747129、化合物

HRID 266463ノート

反応式

HRID 266463 の反応式
C([N:8]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14]([O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])=[CH:15][CH:16]=2)[S:9]1(=[O:11])=[O:10])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[NH4+:8].[CH3:27][O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][C:14]1[CH:13]=[C:12]2[C:17]([C:18](=[O:19])[NH:8][S:9]2(=[O:11])=[O:10])=[CH:16][CH:15]=1

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 70051691HCID 70051691、化合物

生成物 1

HCID 86747129HCID 86747129、化合物

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A mixture of 2-benzyl-6-[2-(2-methoxyethoxy)-ethoxy]saccharin (2.05 g), methanol (75-100 mL), ammonium formate (1.10 g) and palladium on carbon (10%, 1.0 g) was heated under reflux for 40 minutes, allowed to cool and filtered. The filtrate was stripped of volatiles affording 6-[2-(2-methoxyethoxy)-ethoxy]saccharin ammonium salt, a mixture of which with chloromethyl phenyl sulfide (0.79 g) and dimethylformamide was heated for eight hours at 100° C., stirred overnight at room temperature, and poured into ice-water (600 mL). The resulting mixture was extracted with dichloromethane. The dichloromethane extract was washed with water and saturated aqueous sodium chloride solution, dried over sodium sulfate and stripped of dichloromethane. Column chromatography of the residue (1.70 g) on silica gel using dichloromethane-acetone (98:2) as eluant and again using dichloromethane-acetone (99:1) as eluant afforded 2-phenylthiomethyl-6-[2-(2-methoxyethoxy)-ethoxy]saccharin (0.96 g, 45% yield).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 40 minutes
  3. temperatureto cool
  4. filtrationfiltered

出典と根拠

ORDレコード
ord-52ac9e1165114bcf9947d7665d28de89
出典データセット
uspto-grants-1997_07
特許番号
US05650422

反応ノート

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