Bromine → N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]phenyl}-3-(1-cyano-1-methylethyl)benzamide

HRID 2190394노트

반응식

HRID 2190394 반응식
[S-:1][C:2]#[N:3].[K+].[NH2:5][C:6]1[CH:32]=[CH:31][C:9]([O:10][C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:30])[C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([C:28]#[N:29])([CH3:27])[CH3:26])[CH:20]=3)[CH:14]=[CH:15][CH:16]=2)=[CH:8][CH:7]=1.BrBr>C(O)(=O)C>[NH2:3][C:2]1[S:1][C:7]2[CH:8]=[C:9]([O:10][C:11]3[CH:12]=[C:13]([NH:17][C:18](=[O:30])[C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([C:28]#[N:29])([CH3:26])[CH3:27])[CH:20]=4)[CH:14]=[CH:15][CH:16]=3)[CH:31]=[CH:32][C:6]=2[N:5]=1

참가 물질

5

반응물 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 57386827HCID 57386827, 화합물

생성물 1

HCID 57387331N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]phenyl}-3-(1-cyano-1-methylethyl)benzamide수율 87.2%

시약·촉매·용매 1

HCID 176Acetic Acid용매3회

실험 절차

To a solution of potassium thiocyanate (8.09 g, 83.2 mmol) in acetic acid (150 ml) was added a solution of N-[3-(4-aminophenoxy)phenyl]-3-(1-cyano-1-methylethyl)benzamide (7.34 g, 19.8 mmol) in acetic acid (150 ml), and the mixture was stirred at room temperature for 15 min. To the obtained solution was added dropwise a solution of bromine (4.0 g, 25.0 mmol) in acetic acid (100 mL) at room temperature over 30 min or longer and, after the completion of the dropwise addition, the mixture was stirred at room temperature for 4 hr. The resulting yellow solid was filtered off, and the filtrate was concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (100 mL) and ethyl acetate (200 mL), and basified with 2N aqueous sodium hydroxide solution. The aqueous layer was separated and the organic layer was washed with saturated aqueous ammonium chloride solution (200 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (7.4 g, 87%) as a yellow amorphous substance. The obtained compound was used in the next reaction without a further purification.

후처리

  1. additionafter the completion of the dropwise addition
  2. stirringthe mixture was stirred at room temperature for 4 hr
  3. filtrationThe resulting yellow solid was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in tetrahydrofuran (100 mL)
  6. customThe aqueous layer was separated
  7. washthe organic layer was washed with saturated aqueous ammonium chloride solution (200 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationThe insoluble material was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-99be044498ca4da29663578cbc6790ab
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324395B2

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