Water → 3-isopropyl-3-methyl-3H-imidazo[2,1-a]isoindole-2,5-dione

HRID 328360

反応式

HRID 328360 の反応式
[CH:1]([C:4]([CH3:19])([N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=O)[C:5]([NH2:7])=[O:6])([CH3:3])[CH3:2].O.CCCCCC>C1(C)C=CC=CC=1>[CH:1]([C:4]1([CH3:19])[N:8]2[C:16](=[O:17])[C:15]3[C:10]([C:9]2=[N:7][C:5]1=[O:6])=[CH:11][CH:12]=[CH:13][CH:14]=3)([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 962WaterHCID 8058HexaneHCID 4916589alpha-Isopropyl-alpha-methyl-1,3-dioxo-2-isoindolineacetamide

生成物 1

HCID 27292473-isopropyl-3-methyl-3H-imidazo[2,1-a]isoindole-2,5-dione収率 81.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

A solution of 130.1 g (0.5 mole) of α-isopropyl-α-methyl-1,3-dioxo-2-isoindolineacetamide in 650 ml toluene is heated with vigorous stirring under a Dean-Stark water separator in order to remove traces of water. The solution was cooled to 100° C and 2.0 g sodium hydroxide in the form of pels is added and the mixture rapidly heated to reflux. Water collects in the water separator. One-half hour after the addition of the sodium hydroxide, a further 2 g is added and heating is continued for a further 11/4 hours when no further water is removed from the reaction mixture and the infrared spectrum of an aliquot indicates the reaction to be complete. The reaction mixture is cooled to room temperature, filtered and the solids washed with toluene and the toluene removed in vacuo to leave a white solid which is transferred to a filter funnel with hexane and air-dried to give 98.7 g of 3-isopropyl-3-methyl-3H-imidazo[2,1-a]isoindole-2,5-dione, melting point 93°-96° C. The product may be purified by recrystallization from hexane to give an analytically pure sample, melting point 98°-100.5° C.

後処理

  1. customto remove traces of water
  2. addition2.0 g sodium hydroxide in the form of pels is added
  3. temperaturethe mixture rapidly heated to reflux
  4. additionOne-half hour after the addition of the sodium hydroxide
  5. additiona further 2 g is added
  6. temperatureheating
  7. custom4 hours when
  8. customis removed from the reaction mixture
  9. customthe reaction
  10. temperatureThe reaction mixture is cooled to room temperature
  11. filtrationfiltered
  12. washthe solids washed with toluene
  13. customthe toluene removed in vacuo
  14. customto leave a white solid which
  15. customair-dried

出典と根拠

ORDレコード
ord-1d50c0958c4d4d41949ae4f0571ae45b
出典データセット
uspto-grants-1977_04
特許番号
US04017510

関連ノート

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