Salicylamide → 5-Chloro-2-[(1-methyl-3-pyrrolidinyl)oxy]benzamide hemihydrate

HRID 247249

反応式

HRID 247249 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[C:8]([C:9]([NH2:11])=[O:10])[C:7]([OH:13])=[CH:6][CH:5]=1.C(N)(=O)C1C(=CC=CC=1)O.Br[CH:25]1[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26]1>CN(C)C=O.O>[OH2:10].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:13][CH:25]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26]2)=[C:8]([CH:12]=1)[C:9]([NH2:11])=[O:10].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:13][CH:25]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26]2)=[C:8]([CH:12]=1)[C:9]([NH2:11])=[O:10]

参加物

7

反応物 4

HCID 5147SalicylamideHCID 24758Sodium hydrideHCID 3480945-Chloro-2-hydroxybenzamideHCID 137262793-Bromo-1-methylpyrrolidine

生成物 1

HCID 703936985-Chloro-2-[(1-methyl-3-pyrrolidinyl)oxy]benzamide hemihydrate収率 34.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒3 回

実験手順

To a cooled suspension of 2.4 g (0.41 mole) sodium hydride in 50 ml of dimethylformamide was added dropwise 17 g (0.1 mole) of 5-chlorosalicylamide dissolved in 50 ml of dimethylformamide at a rate such that the temperature did not exceed 20° C. After addition of the salicylamide was complete, 16.7 g (0.1 mole) of 3-bromo-1-methylpyrrolidine dissolved in 50 ml of dimethylformamide was added dropwise. The reaction mixture was stirred and heated at reflux for 19 hr. The cooled solution was diluted with 250 ml of water and extracted twice with 250 ml portions of chloroform. The chloroform was extracted thrice with 500 ml portions of 3N hydrochloric acid. The aqueous extracts were made alkaline with 50% sodium hydroxide and extracted with ethyl acetate. Drying over magnesium sulfate and evaporation of the ethyl acetate under reduced pressure gave 6 g (23%) of product as a beige solid. The solid was recrystallized from ethyl acetate, m.p. 126°-128° C.

後処理

  1. customdid not exceed 20° C
  2. additionwas added dropwise
  3. temperatureheated
  4. temperatureat reflux for 19 hr
  5. extractionextracted twice with 250 ml portions of chloroform
  6. extractionThe chloroform was extracted thrice with 500 ml portions of 3N hydrochloric acid
  7. extractionextracted with ethyl acetate
  8. dry with materialDrying over magnesium sulfate and evaporation of the ethyl acetate under reduced pressure

出典と根拠

ORDレコード
ord-c1213d82102941b990e8fde8dc761705
出典データセット
uspto-grants-1987_11
特許番号
US04705853

関連ノート

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