Hexamethylphosphoramide → Methyl 4-cyano-3-nitrobenzoate

HRID 1844783ノート

反応式

HRID 1844783 の反応式
I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][N:16](C)P(=O)(N(C)C)N(C)C>>[C:15]([C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13])#[N:16]

参加物

3

反応物 2

HCID 12679HexamethylphosphoramideHCID 297884Methyl 4-iodo-3-nitrobenzoate

生成物 1

HCID 53419688Methyl 4-cyano-3-nitrobenzoate収率 80.4%

反応条件

温度
100 °C

実験手順

5 g (0.016 mol) Methyl 4-iodo-3-nitrobenzoate (Compound IV-1), 1.77 g (0.02 mol) cuprous cyanide and 15 ml hexamethylphosphoric triamide were added into a reaction flask, and heated to 100° C. and reacted for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, then extracted with 100 ml ethyl acetate, and the organic layer was washed with water for three times, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness, separated by column chromatography to obtain methyl 4-cyano-3-nitrobenzoate (Compound II-8), 2.7 g (0.013 mol), yield 80.4%.

後処理

  1. customreacted for 1 hour
  2. temperaturethe mixture was cooled to room temperature
  3. extractionextracted with 100 ml ethyl acetate
  4. washthe organic layer was washed with water for three times
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated to dryness
  8. customseparated by column chromatography

出典と根拠

ORDレコード
ord-66f4b5b90a1a4a659c1917621c48b0d0
出典データセット
uspto-grants-2015_02
特許番号
US08946478B2

反応ノート

読み込み中…