Diethyl dithiophosphate, potassium salt → 2'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester

HRID 1519255ノート

反応式

HRID 1519255 の反応式
P(OCC)(OCC)([S-])=[S:2].[CH3:10][O:11][C:12]([C:14]1[C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N+:28]([O-:30])=[O:29])=[CH:16][CH:17]=[C:18]([C:20]#[N:21])[CH:19]=1)=[O:13]>C1COCC1.O>[CH3:10][O:11][C:12]([C:14]1[C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N+:28]([O-:30])=[O:29])=[CH:16][CH:17]=[C:18]([C:20](=[S:2])[NH2:21])[CH:19]=1)=[O:13]

参加物

5

反応物 2

HCID 1385274Diethyl dithiophosphate, potassium saltHCID 866798314-Cyano-2'-nitro-biphenyl-2-carboxylic acid methyl ester2 回

生成物 1

HCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester収率 52%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

O,O′-Diethyl dithiophosphate (available from Aldrich Chemical Company, Inc.; 6.85 g, 36.8 mmol) was added to a solution of compound 4-cyano-2′-nitro-biphenyl-2-carboxylic acid methyl ester (which may be prepared as described for Intermediate 3; 8.62 g, 30.5 mmol) in a mixture of THF (96 mL) and water (24 mL). The resulting mixture was stirred at 80° C. for 45 h and then evaporated to a small volume. Ethyl acetate (500 mL) was added and the mixture was washed with water (250 mL) and sat. NaHCO3 (250 mL), dried over anhydrous sodium sulfate, filtered, evaporated, and purified by silica gel chromatography, using 17-50% ethyl acetate/petroleum ether as eluent, to give 2′-nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester (5.0 g, 52%). 1H NMR (300 MHz, CDCl3) δ 8.50 (d, J=2.1 Hz, 1H), 8.18-8.15 (m, 2H), 7.70-7.54 (m, 3H), 7.32 (s, 1H), 7.30 (s, 1H), 7.24 (d, J=1.2 Hz, 1H), 3.69 (s, 3H).

後処理

  1. customevaporated to a small volume
  2. additionEthyl acetate (500 mL) was added
  3. washthe mixture was washed with water (250 mL) and sat. NaHCO3 (250 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-f807f09ddd5143e3810c0ecbe0c00424
出典データセット
uspto-grants-2015_07
特許番号
US09073881B2

反応ノート

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