Water → HCID 178440789、化合物

HRID 1078206ノート

反応式

HRID 1078206 の反応式
[C:1]([C:5]1[CH:6]=[C:7]([CH:23]=[C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:25]=1[OH:26])[CH:8]=[C:9]1[C:14](=[O:15])[N:13]([CH2:16][C:17]#[N:18])[C:12]2[CH:19]=[CH:20][CH:21]=[CH:22][C:11]=2[S:10]1)([CH3:4])([CH3:3])[CH3:2].[N-:31]=[N+:32]=[N-:33].[Na+].[Cl-].[NH4+].O>CC(C)=O>[C:1]([C:5]1[CH:6]=[C:7]([CH:23]=[C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:25]=1[OH:26])[CH:8]=[C:9]1[C:14](=[O:15])[N:13]([CH2:16][C:17]2[NH:33][N:32]=[N:31][N:18]=2)[C:12]2[CH:19]=[CH:20][CH:21]=[CH:22][C:11]=2[S:10]1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 54061185HCID 54061185、化合物

生成物 1

HCID 178440789HCID 178440789、化合物収率 56.9%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
105 °C

実験手順

To a solution of 2-(3,5-di-tert.-butyl-4-hydroxybenzylidene) -4-cyanomethyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazine (compound No. 1-1, 0.335 g) in dimethylformaldehyde (5 ml), sodium azide (0.078 g) and ammonium chloride (0.064 g) were added. The mixture was stirred overnight at 105° C. under a nitrogen atmosphere. To the mixture, water was added, and the whole was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. To the oily residue, 1N aqueous sodium hydroxide solution was added. The mixture was washed with diethyl ether, acidified with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue was purified by silica gel column chromatography to give 0.21 g (56.9%) of the titled compound.

後処理

  1. extractionthe whole was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. additionTo the oily residue, 1N aqueous sodium hydroxide solution was added
  5. washThe mixture was washed with diethyl ether
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe oily residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-4abd2381923847feab648a528e381c46
出典データセット
uspto-grants-1996_08
特許番号
US05547952

反応ノート

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