Diglyme → HCID 178486136、化合物

HRID 2423253ノート

反応式

HRID 2423253 の反応式
[CH3:1][N:2]([CH3:15])[S:3]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9](Cl)=[O:10])(=[O:5])=[O:4].[F:16][C:17]1[CH:18]=[C:19]([C:24](=[O:35])[CH:25]=[C:26]2[NH:30][C:29]3[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=3[NH:27]2)[CH:20]=[C:21]([F:23])[CH:22]=1.C(N(CC)CC)C.COCCOCCOC>O>[F:16][C:17]1[CH:18]=[C:19]([C:24](=[O:35])[C:25](=[C:26]2[NH:27][C:28]3[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=3[NH:30]2)[C:9]([C:8]2[CH:7]=[C:6]([S:3]([N:2]([CH3:15])[CH3:1])(=[O:5])=[O:4])[CH:14]=[CH:13][CH:12]=2)=[O:10])[CH:20]=[C:21]([F:23])[CH:22]=1

参加物

6

反応物 4

HCID 8150DiglymeHCID 8471TriethylamineHCID 188018843-(Dimethylsulfamoyl)benzoyl chlorideHCID 178520380CID 67243546

生成物 1

HCID 178486136HCID 178486136、化合物収率 25.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
110 °C

実験手順

3-[(dimethylamino)sulfonyl]benzoyl chloride (1.97 g) was added to a mixture of 1-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)ethanone (865 mg), triethylamine (1.6 mL) and 2-methoxyethyl ether (10 mL), followed by heating with stirring at 110° C. for 30 minutes. Water (0.06 mL) was added, followed by further heating under reflux for 30 minutes. After cooling, water was added, followed by extraction with ethyl acetate. The organic layer was washed with water, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1), and recrystallized from ethyl acetate/n-hexane to obtain 3-[3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxopropanoyl]-N,N-dimethylbenzenesulfonamide (391 mg).

後処理

  1. temperatureby heating
  2. temperatureby further heating
  3. temperatureunder reflux for 30 minutes
  4. temperatureAfter cooling
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with water
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1)
  9. customrecrystallized from ethyl acetate/n-hexane

出典と根拠

ORDレコード
ord-c15fb3922011467d92f05f3b699caebd
出典データセット
uspto-grants-2011_06
特許番号
US07960562B2

反応ノート

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