Water → 1-[(4-Bromophenyl)methyl]-2-imidazolidinone

HRID 1580122노트

반응식

HRID 1580122 반응식
[NH:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].C([O-])([O-])=O.[K+].[K+].[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1.O>CS(C)=O>[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][N:1]2[CH2:5][CH2:4][NH:3][C:2]2=[O:6])=[CH:16][CH:15]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 84532-ImidazolidinoneHCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromide

생성물 1

HCID 215651691-[(4-Bromophenyl)methyl]-2-imidazolidinone수율 100%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A 12.4 g (0.14 mole) portion of 2-imidazolidinone in 125 ml of dimethylsulfoxide treated with 19.9 g (0.14 mole) of K2CO3, 11.5 g (0.069 mole) of KI and 36.0 g (0.14 mole) of 4-bromobenzylbromide. The reaction mixture was heated to 105° over 0.3 hours, held at 105° with stirring for 1.8 hours, and poured into 1.51 of cold water. The aqueous mixture was extracted with 1.3 l of chloroform. The chloroform extract was washed with 500 ml of water, dried over MgSO4 overnight and filtered. The filtrate was concentrated under reduced pressure to give 36 g (100%) of a light yellow semisolid. The crude product was crystallized using 150 ml of ether, filtered, air dried and dried at 60° for 4 hours to give 15 (42%) of a white solid m.p. 163°-167°. Recrystallization from acetonitrile gave an analytical sample, m.p. 166°-168°.

후처리

  1. temperatureThe reaction mixture was heated to 105° over 0.3 hours
  2. customheld at 105°
  3. extractionThe aqueous mixture was extracted with 1.3 l of chloroform
  4. extractionThe chloroform extract
  5. washwas washed with 500 ml of water
  6. dry with materialdried over MgSO4 overnight
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-9380dde7fbfe4573a8de5baa399f752d
출처 데이터셋
uspto-grants-1976_01
특허 번호
US03932452

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