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

HRID 455179

反応式

HRID 455179 の反応式
[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]

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0bdc90c51b1e440aa85823e68eb7cc67
出典データセット
uspto-grants-2013_07
特許番号
US08497274B2

関連ノート

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