Lithium hydroxide, monohydrate → N-[6-(3-aminophenoxy)-7-cyano-1,3-benzothiazol-2-yl]acetamide

HRID 455179

반응식

HRID 455179 반응식
[C:1]([NH:4][C:5]1[S:6][C:7]2[C:13]([C:14]#[N:15])=[C:12]([O:16][C:17]3[CH:18]=[C:19]([NH:23]C(=O)C(F)(F)F)[CH:20]=[CH:21][CH:22]=3)[CH:11]=[CH:10][C:8]=2[N:9]=1)(=[O:3])[CH3:2].O.[OH-].[Li+]>O1CCCC1.CO.O.C(OCC)(=O)C>[NH2:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[O:16][C:12]1[CH:11]=[CH:10][C:8]2[N:9]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][C:7]=2[C:13]=1[C:14]#[N:15]

참가 물질

7

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 86644687N-(3-{[2-(Acetylamino)-7-cyano-1,3-benzothiazol-6-yl]oxy}phenyl)-2,2,2-trifluoroacetamide

생성물 1

HCID 86644686N-[6-(3-aminophenoxy)-7-cyano-1,3-benzothiazol-2-yl]acetamide수율 38.1%

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

N-(3-{[2-(Acetylamino)-7-cyano-1,3-benzothiazol-6-yl]oxy}phenyl)-2,2,2-trifluoroacetamide (6.8 g, 16.2 mmol) was dissolved in a mixed solvent of tetrahydrofuran (75 mL)/methanol (25 mL)/water (25 mL), lithium hydroxide monohydrate (1.99 g, 48.5 mmol) was added, and the mixture was stirred at room temperature for 20 hr. The reaction mixture was diluted with ethyl acetate (600 mL) and tetrahydrofuran (200 mL), washed successively with 5% aqueous sodium hydrogen carbonate solution (300 mL) and saturated brine (300 mL), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was suspended in N,N-dimethylformamide/ethyl acetate (1:1), and the insoluble material was collected by filtration to give the title compound (2.00 g, 38%) as a white powder.

후처리

  1. additionwas added
  2. washwashed successively with 5% aqueous sodium hydrogen carbonate solution (300 mL) and saturated brine (300 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationInsoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. filtrationthe insoluble material was collected by filtration

출처 및 근거

ORD 기록
ord-0bdc90c51b1e440aa85823e68eb7cc67
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497274B2

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