Sulfuric Acid → 4-[(cyclohexylamino)methyl]-3,3-diphenyldihydro-2(3H)-furanone

HRID 2285768ノート

反応式

HRID 2285768 の反応式
[CH:1]1([N:7]2[CH2:10][CH:9]([C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:12]#N)[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(=O)(=O)(O)[OH:27].[OH-:31].[Na+]>>[CH:1]1([NH:7][CH2:8][CH:9]2[CH2:10][O:31][C:12](=[O:27])[C:11]2([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

4

反応物 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 12822284alpha-(1-Cyclohexyl-3-azetidinyl)-alpha,alpha-diphenylacetonitrile

生成物 1

HCID 128222864-[(cyclohexylamino)methyl]-3,3-diphenyldihydro-2(3H)-furanone収率 20%

反応条件

温度
120 °C

実験手順

To 41.0 g. (0.12 mole) of α-(1-cyclohexyl-3-azetidinyl)-α,α-diphenylacetonitrile was added 100 g. of a 70% solution of sulfuric acid, and the mixture was stirred and heated at 120° C. for 48 hrs. The solution was then poured over ice and made basic with 50% sodium hydroxide, and extracted with chloroform. The organic layer was dried, filtered, and concentrated in vacuo. The residue was crystallized twice from isopropyl ether, the crystallized material weighed 8.0 g. (20% yield) and melted at 129°-131° C.

後処理

  1. additionThe solution was then poured over ice
  2. extractionextracted with chloroform
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized twice from isopropyl ether

出典と根拠

ORDレコード
ord-770240a822554d0cadfd74992670b5b7
出典データセット
uspto-grants-1982_04
特許番号
US04324791

反応ノート

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