Water → HCID 86734553、化合物

HRID 597049

反応式

HRID 597049 の反応式
[H-].[Na+].[CH3:3][C:4]1[NH:5][C:6]2[C:11]([C:12]=1[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][C:9]([O:19][CH3:20])=[CH:8][CH:7]=2.Cl[C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=[CH:24][N:23]=1.O>CN(C)C=O>[CH3:20][O:19][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]([C:22]1[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[CH:24][N:23]=1)[C:4]([CH3:3])=[C:12]2[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 788644-ChloroquinazolineHCID 10729163Ethyl (5-methoxy-2-methyl-1H-indol-3-yl)acetate

生成物 1

HCID 86734553HCID 86734553、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

A stirred suspension of sodium hydride (0.24g.) in dry dimethylformamide (20ml.; dried with calcium hydride) was treated at 5°-10° C. with a solution of ethyl 2-methyl-5-methoxyindol-3-ylacetate (2.3g.) in dry dimethylformamide (10ml.). The mixture was stirred at 25°-30° C. for 15 minutes, and the solution obtained was treated with a freshly prepared solution of 4-chloroquinazoline (1.65g.) in dry dimethylformamide (10ml.). The mixture was stirred at 30°-40° C, for 4 hours, and then poured into water (500ml.). The mixture was extracted with ethyl acetate (4 × 100ml.) and the extracts washed successively with water (2 × 100ml.) and brine (100ml.), and then dried (sodium sulphate). Evaporation of solvent gave an oil which was purified by chromatography on silica gel (250g.) using an increasing gradient of ether in petroleum ether (b.p. 40°-60° C.) (the polarity increased by incremental addition of 10% v/v ether) to give ethyl 5-methoxy-2-methyl-1-(quinazolin-4-yl)indol-3-ylacetate, m.p. 121°-123° C.

後処理

  1. customthe solution obtained
  2. stirringThe mixture was stirred at 30°-40° C, for 4 hours
  3. extractionThe mixture was extracted with ethyl acetate (4 × 100ml.)
  4. washthe extracts washed successively with water (2 × 100ml.) and brine (100ml.)
  5. dry with materialdried (sodium sulphate)
  6. customEvaporation of solvent
  7. customgave an oil which
  8. customwas purified by chromatography on silica gel (250g.)
  9. temperatureincreased by incremental addition of 10% v/v ether)

出典と根拠

ORDレコード
ord-d95b3c6698a1461090a0654bfd792439
出典データセット
uspto-grants-1977_03
特許番号
US04012513

関連ノート

読み込み中…