Ammonia → 4-Carbamoylmethyl-2-(3,5-di-tert.-butyl-4-hydroxybenzylidene)-3,4-dihydro-3-oxo-2H-1,4-benzothiazine

HRID 1439842ノート

反応式

HRID 1439842 の反応式
Cl.[C:2]([C:6]1[CH:7]=[C:8]([CH:27]=[C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:29]=1[OH:30])[CH:9]=[C:10]1[C:15](=[O:16])[N:14]([CH2:17][C:18]([O:20]CC)=O)[C:13]2[CH:23]=[CH:24][CH:25]=[CH:26][C:12]=2[S:11]1)([CH3:5])([CH3:4])[CH3:3].[NH3:35]>CO>[C:18]([CH2:17][N:14]1[C:13]2[CH:23]=[CH:24][CH:25]=[CH:26][C:12]=2[S:11][C:10](=[CH:9][C:8]2[CH:27]=[C:28]([C:31]([CH3:33])([CH3:32])[CH3:34])[C:29]([OH:30])=[C:6]([C:2]([CH3:3])([CH3:5])[CH3:4])[CH:7]=2)[C:15]1=[O:16])(=[O:20])[NH2:35]

参加物

5

反応物 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 573062862-(3,5-di-tert.-butyl-4-hydroxybenzylidene)-3,4-dihydro-4-ethoxycarbonylmethyl-3-oxo-2H-1,4-benzothiazine

生成物 1

HCID 867493044-Carbamoylmethyl-2-(3,5-di-tert.-butyl-4-hydroxybenzylidene)-3,4-dihydro-3-oxo-2H-1,4-benzothiazine収率 37.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
80 °C

実験手順

0.1N hydrochloric acid in methanol (3 ml) was added to a solution of 2-(3,5-di-tert.-butyl-4-hydroxybenzylidene)-3,4-dihydro-4-ethoxycarbonylmethyl-3-oxo-2H-1,4-benzothiazine (Compound No. 1-1, 0.4 g) in 17.85 N ammonia in methanol (15 ml). After the addition, the mixture was stirred for 4 days at 80° C. in a sealed tube and followed by concentration in vacuo. To the residue, dilute hydrochloric acid was added and the whole was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue was purified by silica gel column chromatography to give 0.14 g (37.3%) of the titled compound.

後処理

  1. additionAfter the addition
  2. concentrationfollowed by concentration in vacuo
  3. additionTo the residue, dilute hydrochloric acid was added
  4. extractionthe whole was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe oily residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-17e4048fb86340c8bcc37b1620311e75
出典データセット
uspto-grants-1996_03
特許番号
US05496817

反応ノート

読み込み中…