Triethylamine → 3-(7-Chloro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methylimidazolidine-2,4-dione

HRID 344605ノート

反応式

HRID 344605 の反応式
Cl.C(O[C:5](=[O:9])[CH2:6][NH:7][CH3:8])C.[Cl:10][C:11]1[C:19]2[O:18][CH:17]([CH3:20])[CH2:16][C:15]=2[C:14]([N:21]=[C:22]=[O:23])=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:10][C:11]1[C:19]2[O:18][CH:17]([CH3:20])[CH2:16][C:15]=2[C:14]([N:21]2[C:5](=[O:9])[CH2:6][N:7]([CH3:8])[C:22]2=[O:23])=[CH:13][CH:12]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 537184027-Chloro-2,3-dihydro-4-isocyanato-2-methylbenzofuran

生成物 1

HCID 679267013-(7-Chloro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methylimidazolidine-2,4-dione

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

2.30 g of sarcosine ethyl ester hydrochloride was added over 5 minutes to a mixture of 2.10 g of 34A, 1.52 g of triethylamine and 60 mL of methylene chloride, under nitrogen at 25°-30° C. The mixture was stirred at room temperature for 24 hours, then diluted with 100 mL of methylene chloride, washed with water, then brine, dried (MgSO4) and stripped of solvent. The residue was dissolved in 70 mL of a 1:1 v:v mixture of ethanol and 2N hydrochloric acid. The solution was refluxed for 4 hours, the resulting mixture was stirred at room temperature overnight, stripped of volatiles, diluted with water and extracted with methylene chloride. The extract was dried (MgSO4) and stripped of solvent. The residue was purified by flash chromatography over silica gel with a 1:2 v:v mixture of hexane and ethyl acetate as eluent to give the title compound, as a glass/sticky solid.

後処理

  1. washwashed with water
  2. dry with materialbrine, dried (MgSO4)
  3. dissolutionThe residue was dissolved in 70 mL of a 1:1 v
  4. additionv mixture of ethanol and 2N hydrochloric acid
  5. temperatureThe solution was refluxed for 4 hours
  6. stirringthe resulting mixture was stirred at room temperature overnight
  7. additiondiluted with water
  8. extractionextracted with methylene chloride
  9. dry with materialThe extract was dried (MgSO4)
  10. customThe residue was purified by flash chromatography over silica gel with a 1:2 v
  11. additionv mixture of hexane and ethyl acetate as eluent

出典と根拠

ORDレコード
ord-33f88dda2cf54fee96cdf41723b674e9
出典データセット
uspto-grants-1991_10
特許番号
US05053071

反応ノート

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