Formaldehyde → 5-dimethylaminomethyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one hydrochloride

HRID 1728920ノート

反応式

HRID 1728920 の反応式
[ClH:1].[CH3:2][NH:3][CH3:4].[CH2:5]=O.[S:7]1[C:11]2[S:12][CH2:13][CH2:14][C:15](=[O:16])[C:10]=2[CH:9]=[CH:8]1>C(OC(=O)C)(=O)C>[ClH:1].[CH3:2][N:3]([CH2:5][CH:14]1[CH2:13][S:12][C:11]2[S:7][CH:8]=[CH:9][C:10]=2[C:15]1=[O:16])[CH3:4]

参加物

5

反応物 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 110302745,6-Dihydro-4H-thieno[2,3-b]thiopyran-4-one

生成物 1

HCID 126753075-dimethylaminomethyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one hydrochloride収率 69.3%

試薬・触媒・溶媒 1

HCID 7918Acetic Anhydride溶媒

反応条件

温度
70 °C

実験手順

A mixture of 18 g of dimethylamine hydrochloride and 18 g of 37% formalin is stirred for 30 minutes and the temperature of the mixture is raised to 70° C. To the mixture is added 80 ml of acetic anhydride dropwise for 20 minutes at 70°-80° C. and kept for about 20 minutes at the same temperature. To the mixture is added 32.6 g of 5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one. The mixture is kept for 4 hours at the same temperature and then the solvent is distilled off under reduced pressure. To the residue is added acetone, and the precipitated crystals are collected by filtration and recrystallized from a mixed solvent of ethanol and isopropyl ether to give 35 g of 5-dimethylaminomethyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one hydrochloride as white crystals, melting at 163°-166° C.

後処理

  1. waitkept for about 20 minutes at the same temperature
  2. waitThe mixture is kept for 4 hours at the same temperature
  3. distillationthe solvent is distilled off under reduced pressure
  4. additionTo the residue is added acetone
  5. filtrationthe precipitated crystals are collected by filtration
  6. customrecrystallized from a mixed solvent of ethanol and isopropyl ether

出典と根拠

ORDレコード
ord-8dd91ade7da445c18d966d4554b5290d
出典データセット
uspto-grants-1994_07
特許番号
US05329016

反応ノート

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