Ethylamine hydrochloride → N-(4-chloro-3-methylisothiazol-5-yl)-alpha-[(ethylamino)methylene]-[2-(2,2-dimeth-ylpropyl)benzoxazol-5-yl]acetamide

HRID 48153

反応式

HRID 48153 の反応式
[Cl:1][C:2]1[C:3]([CH3:29])=[N:4][S:5][C:6]=1[NH:7][C:8](=[O:28])[C:9]([C:14]1[CH:15]=[CH:16][C:17]2[O:21][C:20]([CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[N:19][C:18]=2[CH:27]=1)=[CH:10][N:11]([CH3:13])C.Cl.[CH2:31](N)C>O1CCCC1.O>[Cl:1][C:2]1[C:3]([CH3:29])=[N:4][S:5][C:6]=1[NH:7][C:8](=[O:28])[C:9]([C:14]1[CH:15]=[CH:16][C:17]2[O:21][C:20]([CH2:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[N:19][C:18]=2[CH:27]=1)=[CH:10][NH:11][CH2:13][CH3:31]

参加物

5

反応物 2

HCID 11198Ethylamine hydrochlorideHCID 69548266N-(4-chloro-3-methylisothiazol-5-yl)-alpha-[(dimethylamino)methylene]-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]acetamide

生成物 1

HCID 69548595N-(4-chloro-3-methylisothiazol-5-yl)-alpha-[(ethylamino)methylene]-[2-(2,2-dimeth-ylpropyl)benzoxazol-5-yl]acetamide収率 85.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

A mixture of N-(4-chloro-3-methylisothiazol-5-yl)-α-[(dimethylamino)methylene]-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]acetamide (0.20 g, 0.00046 mole) [from Example 5] and ethylamine hydrochloride (0.0225 g, 0.0028 mole) in tetrahydrofuran (4 ml) and water (1 ml) was heated for 24 hours at 60° C. The mixture was cooled to room temperature, the solvent was evaporated in vacuo and the residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic extract was dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. Further purification by flash column chromatography, eluting with ethyl acetate:hexane at 2:3 by volume, gave N-(4-chloro-3-methylisothiazol-5-yl)-α-[(ethylamino)methylene]-[2-(2,2-dimeth-ylpropyl)benzoxazol-5-yl]acetamide as a colourless solid (0.17 g). Analysis by 1H NMR showed the product comprised a mixture of E- and Z-isomers.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. customthe solvent was evaporated in vacuo
  3. customthe residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate was evaporated in vacuo
  8. customFurther purification by flash column chromatography
  9. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-36922d85c99342c8a3007650d1e96f8c
出典データセット
uspto-grants-2004_03
特許番号
US06703347B2

関連ノート

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