3-(DIMETHYLAMINO)-1-PROPANETHIOL → 1-Propanamine, N,N-dimethyl-3-((2-phenyl-5H-(1)benzopyrano(2,3-d)pyrimidin-4-yl)thio)-

HRID 483080ノート

反応式

HRID 483080 の反応式
[Na].[CH3:2][N:3]([CH3:8])[CH2:4][CH2:5][CH2:6][SH:7].Cl[C:10]1[C:11]2[CH2:25][C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[O:22][C:12]=2[N:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:15]=1>C(O)C>[CH3:2][N:3]([CH3:8])[CH2:4][CH2:5][CH2:6][S:7][C:10]1[C:11]2[CH2:25][C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[O:22][C:12]=2[N:13]=[C:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:15]=1

参加物

5

反応物 3

HCID 30169983-(DIMETHYLAMINO)-1-PROPANETHIOLHCID 5360545SodiumHCID 86740692HCID 86740692、化合物

生成物 1

HCID 134909611-Propanamine, N,N-dimethyl-3-((2-phenyl-5H-(1)benzopyrano(2,3-d)pyrimidin-4-yl)thio)-収率 52%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Eight and one tenth (8.1) gram 4-hydroxy-2-phenyl[1]benzopyrano[2,3-d]pyrimidine, 9.0 g phosphoruspentachloride and 36 ml phosphorusoxychloride are heated for two hours under reflux. Excess phosphorusoxychloride is then distilled off under a vacuum and the residue is partitioned to chloroform and water, a pH 6 value being adjusted by the addition of 10% sodium hydroxide. The organic phase is separated and the chloroform removed by distillation in a rotary evaporator. The residue obtained is separated by chromatography using cyclohexane/chloroform 1:1 as an eluting agent. There are obtained 4.0 g 4-chloro-2-phenyl[1]benzopyrano[2,3-d]pyrimidine, mp 168°-170° C. as colorless crystals. Thereafter 0.05 g sodium are dissolved in 10 ml anhydrous ethanol and 0.25 g 3-dimethylamino-1-propane-thiol added to the solution. The mixture obtained is added dropwise to a solution of 0.6 g 4-chloro-2-phenyl[1]benzopyrano[2,3-d]pyrimidine at reflux temperature. The reaction mixture is then kept under reflux for another two hours. After cooling the reaction mixture is filtered and the filtrate is evaporated to dryness and the residue partitioned to chloroform and water. The organic phase is separated off, the chloroform is evaporated and the residue recrystallized from ethanol. There are obtained 0.4 g colorless crystals, mp 93° C.

後処理

  1. customThe mixture obtained
  2. temperatureat reflux temperature
  3. temperatureunder reflux for another two hours
  4. temperatureAfter cooling the reaction mixture
  5. filtrationis filtered
  6. customthe filtrate is evaporated to dryness
  7. customthe residue partitioned to chloroform and water
  8. customThe organic phase is separated off
  9. customthe chloroform is evaporated
  10. customthe residue recrystallized from ethanol

出典と根拠

ORDレコード
ord-ded157db5cb44ff6ab6ec2211e3dfffb
出典データセット
uspto-grants-1986_03
特許番号
US04578380

反応ノート

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