Methanol → 7-hydroxymethyl-1-isopropyl-4-phenyl-2(1H)-quinazolinone

HRID 461775ノート

反応式

HRID 461775 の反応式
Br[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:8][C:9](=[O:16])[N:10]2[CH:13]([CH3:15])[CH3:14])=[CH:5][CH:4]=1.C(=O)([O-])[O-:24].[Na+].[Na+].CO.[OH-].[Na+]>C(Cl)(Cl)Cl.C1C=CC=CC=1.O>[OH:24][CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:8][C:9](=[O:16])[N:10]2[CH:13]([CH3:15])[CH3:14])=[CH:5][CH:4]=1

参加物

7

反応物 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 213925047-bromomethyl-1-isopropyl-4-phenyl-2(1H)-quinazolinone

生成物 1

HCID 213925057-hydroxymethyl-1-isopropyl-4-phenyl-2(1H)-quinazolinone

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 22101329Benzene--trichloromethane (1/1)溶媒

実験手順

A mixture of 69.3 of crude 7-bromomethyl-1-isopropyl-4-phenyl-2(1H)-quinazolinone (obtained by repeating Step A, above), 500 ml of a 10% aqueous sodium carbonate solution and 500 ml of methanol is refluxed for 8 hours, cooled, diluted by addition of 200 ml of distilled water containing 6 ml of 10N sodium hydroxide solution, and the resulting mixture extracted 3 times each with 400 ml of chloroform. Each extract is then washed twice with 200 ml portions of distilled water. The organic extracts are combined and evaporated to dryness to obtain a residue. The residue, thus obtained, is taken up in 100 ml of a mixture of chloroform: benzene (1:1), which solution is then placed on a chromatographic column of 480 g of silica gel in the same solvent. The column is eluted and fractions of from about 600 to 750 ml taken, in turn with 3 liters of chloroform: benzene (1:1) (fractions 1 to 4); 2 liters of 100% chloroform (fractions 5 to 7); 5 liters of ethyl acetate: chloroform (1:3) (fractions 8 to 14); and lastly 3 liters of ethyl acetate: Chloroform (1:1) (fractions 15 to 18). Fractions 9 to 14 are combined and evaporated to dryness to obtain a residue which yields refined title compound on repeated crystallization from ethyl acetate, m.p. 223° -225°.

後処理

  1. temperatureis refluxed for 8 hours
  2. temperaturecooled
  3. extractionthe resulting mixture extracted 3 times each with 400 ml of chloroform
  4. washEach extract is then washed twice with 200 ml portions of distilled water
  5. customevaporated to dryness
  6. customto obtain a residue
  7. customThe residue, thus obtained
  8. washThe column is eluted
  9. customevaporated to dryness
  10. customto obtain a residue which

出典と根拠

ORDレコード
ord-21055aff072f42cba330a320d52d7c64
出典データセット
uspto-grants-1977_12
特許番号
US04064246

反応ノート

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