Acetic Acid → 2-Amino-6-methylbenzothiazole

HRID 8353

반응식

HRID 8353 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH2:11])=[S:10])=[CH:4][CH:3]=1.CC(O)=O.Br.CS(C)=O>CCOC(C)=O>[NH2:11][C:9]1[S:10][C:6]2[CH:7]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=2[N:8]=1

참가 물질

6

반응물 4

HCID 176Acetic Acid2회HCID 260Hydrogen BromideHCID 679Dimethyl SulfoxideHCID 722833p-Tolylthiourea

생성물 1

HCID 173352-Amino-6-methylbenzothiazole수율 67%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

(4-Methylphenyl)thiourea (2 mmol) was added to AcOH (4 ml), and the suspension was heated to 80° C. To the solution formed was added 33% HBr in AcOH (4 mmol) followed by DMSO (2.1 mmol). After stirring at 80° C. for 1 h, the reaction mixture was cooled to 50° C., diluted with EtOAc (10 ml) and filtered. The product (as HBr-salt) was taken up in H2O (5 ml) and treated with 1M aq. NaHCO3 (2 ml). Stirring was continued for 0.2 h. The precipitated aminobenzothiazole was then filtered, washed with H2O (10 ml) and dried (16 h at 45° C./20 mb); yield 67%.

후처리

  1. customTo the solution formed
  2. temperaturethe reaction mixture was cooled to 50° C.
  3. filtrationfiltered
  4. additiontreated with 1M aq. NaHCO3 (2 ml)
  5. stirringStirring
  6. waitwas continued for 0.2 h
  7. filtrationThe precipitated aminobenzothiazole was then filtered
  8. washwashed with H2O (10 ml)
  9. customdried (16 h at 45° C./20 mb)

출처 및 근거

ORD 기록
ord-2c38c04a2ff54f61871a1c6ab0095848
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087761B2

연결된 노트

불러오는 중…