Hydrochloric Acid → 2-Butyl-3-(4-iodobenzyl)-1,3-diazaspiro[4.4]non-1-en-4-one

HRID 18684

反応式

HRID 18684 の反応式
Cl.[CH2:2]([C:6]1[NH:10][C:9](=[O:11])[C:8]2([CH2:15][CH2:14][CH2:13][CH2:12]2)[N:7]=1)[CH2:3][CH2:4][CH3:5].[OH-].[K+].[I:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O>[CH2:2]([C:6]1[N:10]([CH2:23][C:22]2[CH:25]=[CH:26][C:19]([I:18])=[CH:20][CH:21]=2)[C:9](=[O:11])[C:8]2([CH2:15][CH2:14][CH2:13][CH2:12]2)[N:7]=1)[CH2:3][CH2:4][CH3:5]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 9542584-Iodobenzyl bromideHCID 101765112-Butyl-1,3-diazaspiro[4.4]non-1-en-4-one

生成物 1

HCID 119964262-Butyl-3-(4-iodobenzyl)-1,3-diazaspiro[4.4]non-1-en-4-one収率 88%

試薬・触媒・溶媒 3

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 962Water溶媒2 回HCID 1140Toluene溶媒

反応条件

温度
25 °C

実験手順

A solution of 23.07 g (100 mmol) of the hydrochloride of 2-butyl-1,3-diazaspiro[4,4]non-1-en-4-one and 19.8 g of potassium hydroxide in 100 mL de water is added to a solution of 29.7 g (100 mmol) of 4-iodobenzyl bromide and 3.4 g (10 mmol) of tetrabutylammonium bisulphate in 30 mL of toluene, and the mixture is heated at reflux for 1 hr. After cooling to 25° C., 100 mL of water is added and the phases are separated. To the organic phase is added 10 mL of concentrated hydrochloric acid, 100 mL is evaporated at reduced pressure, 300 mL of ethyl acetate is added and the resulting solid is filtered to give 39.6 g (88%) of the title compound in the form of hydrochloride.

後処理

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 1 hr
  3. customthe phases are separated
  4. additionTo the organic phase is added 10 mL of concentrated hydrochloric acid, 100 mL
  5. customis evaporated at reduced pressure, 300 mL of ethyl acetate
  6. additionis added
  7. filtrationthe resulting solid is filtered

出典と根拠

ORDレコード
ord-cfa93898b13c4cddbdf0bab68e95b661
出典データセット
uspto-grants-2010_06
特許番号
US07741492B2

関連ノート

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