Hydrochloric Acid → (3AS-cis)-1,3-Dibenzyltetrahydro-1H-thieno[3,4-D]imidazole-2,4-dione

HRID 1740486ノート

反応式

HRID 1740486 の反応式
[CH2:1]([N:8]1[C@H:12]2[CH2:13][O:14][C:15](=O)[C@H:11]2[N:10]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].[S].[SH2:31].Cl>[Zn].O.C1(C)C=CC=CC=1>[CH2:1]([N:8]1[C@H:12]2[CH2:13][S:31][C:15](=[O:14])[C@H:11]2[N:10]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 402Hydrogen Sulfide2 回HCID 119819(3AS,6aR)-1,3-dibenzyltetrahydro-1H-furo(3,4-d)imidazole-2,4-dioneHCID 517045Sodium AcetateHCID 5362487Sulfur

生成物 1

HCID 119817(3AS-cis)-1,3-Dibenzyltetrahydro-1H-thieno[3,4-D]imidazole-2,4-dione

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

After heating to 90° C. a mixture of 38.68 g of (+)-cis-1,3-dibenzylhexahydrofuro[3,4-d]imidazole-2,4-dione, 6.04 g of sodium acetate, 2.49 g of sulfur and 47.56 g of polyethylene glycol (the average molecular weight: 600), it was stirred for 4.5 hours at the temperature while blowing 4.50 g of hydrogen sulfide at a rate of 10 ml/minute. Then blowing of hydrogen sulfide was stopped and the resultant mixture was stirred for 5 hours at the temperature. After cooling the reaction mixture to room temperature, 173.61 g of toluene and 99.70 g of water were added to the mixture, and 8.25 g of zinc powder was further added to the mixture while stirring at room temperature. After dropping 54.90 g of 35% hydrochloric acid at the same temperature, the resultant mixture was stirred at 45° C. for 8 hours. The mixture was separated by removing water layer to give an oil layer, which was concentrated to give a product. Recrystallization from 2-propanol and water gave a crystal of (+)-cis-1,3-dibenzylhexahydrothieno[3,4-d]imidazole-2,4-dione. The yield was 36.96 g (yield percentage: 91%). Melting point was 126° C. [α]D20 was 90° C.=1.0; chloroform).

後処理

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. additionwas further added to the mixture
  3. stirringwhile stirring at room temperature
  4. customThe mixture was separated
  5. customby removing water layer
  6. customto give an oil layer, which
  7. concentrationwas concentrated
  8. customto give a product
  9. customRecrystallization from 2-propanol and water

出典と根拠

ORDレコード
ord-81b21340cc9d40309052f93bc1ed2125
出典データセット
uspto-grants-1999_10
特許番号
US05969149

反応ノート

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