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Sodium ethoxide → HCID 178490014、化合物

HRID 1860542
ノート
印刷プレビュー

反応式

HRID 1860542 の反応式
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][C:8]=2[Cl:15])[N:5]=[C:4]([S:16][CH3:17])[C:3]=1[C:18]([NH2:20])=[O:19].[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:29][C:30](Cl)=O)[CH:26]=[CH:27][CH:28]=1.[O-]CC.[Na+]>C(O)C>[Cl:13][C:12]1[CH:11]=[C:10]([Cl:14])[CH:9]=[C:8]([Cl:15])[C:7]=1[N:6]1[C:2]2=[N:1][C:30]([CH2:29][C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([O:22][CH3:21])[CH:24]=3)=[N:20][C:18](=[O:19])[C:3]2=[C:4]([S:16][CH3:17])[NH:5]1
参加物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 2723922Sodium ethoxideHCID 27332463-Methoxyphenylacetyl chlorideHCID 113025915-Amino-3-(methylthio)-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamide

生成物 1

HCID 178490014HCID 178490014、化合物収率 92%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

To a stirred solution of 176 mg (0.5 mmol) of 5-amino-3-(methylthio)-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamide in 6 mL of absolute ethanol was added 550 mg (3.0 mmol) of 3-methoxyphenylacetyl chloride followed by 2.3 mL (6.0 mmol) of 2.66 M sodium ethoxide in ethanol. The solution was stirred 18 h at reflux, and the heating mantle was then removed. The reaction was treated with 5 mL of 10% aq. HOAc, cooled to ambient temperature, and filtered. The filtrate was washed with 6 mL of 1:1 water-methanol then 6 mL of 1:1 ether-hexanes. The off-white solid was briefly air-dried to give 220 mg (92%) of 1-(2,4,6-trichlorophenyl)-3-(methylthio)-6-(3-methoxybenzyl)pyrazolo[3,4-d]pyrimidin-4-one, mp 245-248° C. Mass spec. Calc'd for C20H16N4O2SCl3: 481.0060. Found: 481.0076 (M+H)+.

後処理

  1. temperatureat reflux
  2. customthe heating mantle was then removed
  3. additionThe reaction was treated with 5 mL of 10% aq. HOAc
  4. filtrationfiltered
  5. washThe filtrate was washed with 6 mL of 1:1 water-methanol
  6. customThe off-white solid was briefly air-dried

出典と根拠

ORDレコード
ord-1b9ec58720124479a2519d74375aafea
出典データセット
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06531477B1

反応ノート

読み込み中…

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