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

HRID 364360

반응식

HRID 364360 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-13c4163777ba4598a61f7d24b074232b
출처 데이터셋
uspto-grants-1986_08
특허 번호
US04604388

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