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

HRID 447015ノート

反応式

HRID 447015 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-11fe587a16654129a22189c79c234f8e
出典データセット
uspto-grants-2013_07
特許番号
US08481544B2

反応ノート

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