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

HRID 1580122ノート

反応式

HRID 1580122 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-9380dde7fbfe4573a8de5baa399f752d
出典データセット
uspto-grants-1976_01
特許番号
US03932452

反応ノート

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