p-Anisoyl chloride → HCID 10591644、化合物

HRID 264027

反応式

HRID 264027 の反応式
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:22](Cl)(=[O:31])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1>ClCCl>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([C:22]([NH:14][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:31])=[CH:24][CH:25]=1

参加物

5

反応物 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 68297N-Phenyl-o-phenylenediamine

生成物 1

HCID 10591644HCID 10591644、化合物収率 62.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A vigorously stirring solution of N-phenyl-1,2-phenylenediamine (20.15 g) in dichloromethane (325 ml) and triethylamine (11.07 g) was cooled in an ice/acetone bath under nitrogen. p-Anisoyl chloride (18.66 g) dissolved in dichloromethane (100 ml) was added dropwise over a 20 minute period while maintaining a temperature of <5° C. The reaction mixture was allowed to warm to ambient temperature and stirred for two hours. The organic solution was washed successively with water (200 ml), 2N aqueous HCl (80 ml), and saturated brine solution (160 ml), then dried over sodium sulfate and passed through a pad of silica (150 g). The silica was eluted with ethyl acetate (1 L) and the eluent was evaporated in vacuo to a pink solid. The solid was triturated overnight with ethyl ether (350 ml), cooled in an ice bath, filtered, and dried in vacuo to give the title compound as a light pink solid (21.67 g). 1H (300 MHz, CDCl3): d 3.82 (s, 3H), 5.75 (br s, 1H), 6.80-6.91(m, 5H), 7.12-7.29 (m, 5H), 7.62 (d, J=8.8 Hz, 2H), 8.15 (dd, J=1.7, 7.8 Hz, 1H), 8.36 (s, 1H); TLC (EtOAc/Hex, 1:4): Rf =0.24; m.p.: 148°-150° C.

後処理

  1. additionwas added dropwise over a 20 minute period
  2. temperaturewhile maintaining a temperature of <5° C
  3. washThe organic solution was washed successively with water (200 ml), 2N aqueous HCl (80 ml), and saturated brine solution (160 ml)
  4. dry with materialdried over sodium sulfate
  5. washThe silica was eluted with ethyl acetate (1 L)
  6. customthe eluent was evaporated in vacuo to a pink solid
  7. customThe solid was triturated overnight with ethyl ether (350 ml)
  8. temperaturecooled in an ice bath
  9. filtrationfiltered
  10. customdried in vacuo

出典と根拠

ORDレコード
ord-2f37e187e9c9439e86f918932f20cd67
出典データセット
uspto-grants-1997_07
特許番号
US05646140

関連ノート

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