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

HRID 1439842노트

반응식

HRID 1439842 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-17e4048fb86340c8bcc37b1620311e75
출처 데이터셋
uspto-grants-1996_03
특허 번호
US05496817

반응 노트

불러오는 중…