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Dimethylformamide → N-(4-chloro-3-methylisothiazol-5-yl)-alpha-[(dimethylamino)methylene]-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]acetamide

HRID 48152
ノート
印刷プレビュー

反応式

HRID 48152 の反応式
[Cl:1][C:2]1[C:3]([CH3:25])=[N:4][S:5][C:6]=1[NH:7][C:8](=[O:24])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]2[O:17][C:16]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N:15][C:14]=2[CH:23]=1.CO[CH:28](OC)[N:29]([CH3:31])[CH3:30].CN(C)C=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([CH3:25])=[N:4][S:5][C:6]=1[NH:7][C:8](=[O:24])[C:9]([C:10]1[CH:11]=[CH:12][C:13]2[O:17][C:16]([CH2:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[N:15][C:14]=2[CH:23]=1)=[CH:28][N:29]([CH3:31])[CH3:30]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 22742093N-(4-Chloro-3-methyl-5-isothiazolyl)-2-(2,2-dimethylpropyl)-5-benzoxazoleacetamide

生成物 1

HCID 69548266N-(4-chloro-3-methylisothiazol-5-yl)-alpha-[(dimethylamino)methylene]-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]acetamide収率 27.3%

試薬・触媒・溶媒 1

HCID 1140
Toluene
溶媒

反応条件

温度
110 °C

実験手順

N-(4-Choro-3-methylisothiazol-5-yl)-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]acetamide (2.5 g, 0.0066 mole) [prepared as in Example 1] and N,N-dimethylformamide dimethylacetal (1.5 g, 0.013 mole) were added to a mixture of N,N-dimethylformamide (5 ml) and toluene (20 ml) and the resulting mixture was heated to 110° C. for 4 hours. The mixture as cooled to room temperature and the solvent was evaporated in vacuo. The residue was taken up in ethyl acetate and washed sequentially with brine and water, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo. The residue was further purified by flash column chromatography, eluting with ethyl acetate:hexane at 1:1 by volume. Further flash column chromatography, eluting with ethyl acetate:dichloromethane at 1:9 by volume gave N-(4-chloro-3-methylisothiazol-5-yl)-α-[(dimethylamino)methylene]-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]acetamide (0.78 g) as a single geometrical isomer.

後処理

  1. temperatureThe mixture as cooled to room temperature
  2. customthe solvent was evaporated in vacuo
  3. washwashed sequentially with brine and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate evaporated in vacuo
  7. customThe residue was further purified by flash column chromatography
  8. washeluting with ethyl acetate
  9. washFurther flash column chromatography, eluting with ethyl acetate

出典と根拠

ORDレコード
ord-230e7a6aabbb42c989df738c3d677755
出典データセット
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06703347B2

反応ノート

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