Ammonia → 7-Bromo-5-pyrazol-1-yl-benzothiazol-2-ylamine

HRID 1010647노트

반응식

HRID 1010647 반응식
[Br:1][C:2]1[CH:3]=[C:4]([NH:13][C:14]([NH2:16])=[S:15])[CH:5]=[C:6]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[CH:7]=1.BrBr.N>C(Cl)Cl.O>[Br:1][C:2]1[C:3]2[S:15][C:14]([NH2:16])=[N:13][C:4]=2[CH:5]=[C:6]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[CH:7]=1

참가 물질

6

반응물 3

HCID 222AmmoniaHCID 24408BromineHCID 57813577(3-Bromo-5-pyrazol-1-yl-phenyl)-thiourea

생성물 1

HCID 578136977-Bromo-5-pyrazol-1-yl-benzothiazol-2-ylamine수율 33.9%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a solution of (3-bromo-5-pyrazol-1-yl-phenyl)-thiourea (1.0 g, 3.0 mmol) in DCM (17.0 mL) at 0° C. was added dropwise a solution of Br2 (1.07 g, 6.0 mmol, in 3.0 ml of DCM) over a period of 15 min. The reaction mixture was stirred at 0° C. for 15 min followed by refluxing for 2 h. The reaction mixture was cooled to room temperature and filtered to get the crude residue that was washed with hexane and diethyl ether. The solid thus obtained was dissolved in H2O, basified with aqueous ammonia solution to pH 10-12 and extracted with ethyl acetate (×3). The combined organic was washed with water, dried (Na2SO4), filtered and concentrated. The residue was purified over silica gel (230-400 M, 25% EtOAc-Hexane) to get the desired product (0.30 g, 30%).

후처리

  1. temperatureby refluxing for 2 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. customto get the crude residue that
  5. washwas washed with hexane and diethyl ether
  6. customThe solid thus obtained
  7. extractionextracted with ethyl acetate (×3)
  8. washThe combined organic was washed with water
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified over silica gel (230-400 M, 25% EtOAc-Hexane)

출처 및 근거

ORD 기록
ord-2324ad1b6b52480a89c38e6e90201116
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977340B2

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