Dimethylamine → 5-Butylidene-3-[4-(3-dimethylaminomethylimidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

HRID 357151노트

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HRID 357151 반응식
[CH2:1]=O.[CH3:3][NH:4][CH3:5].[CH:6](=[C:10]1[S:14][C:13](=[O:15])[N:12]([CH2:16][CH2:17][CH2:18][CH2:19][S:20][C:21]2[N:26]3[CH:27]=[CH:28][N:29]=[C:25]3[CH:24]=[CH:23][CH:22]=2)[C:11]1=[O:30])[CH2:7][CH2:8][CH3:9].[OH-].[Na+]>C(O)(=O)C>[CH:6](=[C:10]1[S:14][C:13](=[O:15])[N:12]([CH2:16][CH2:17][CH2:18][CH2:19][S:20][C:21]2[N:26]3[C:27]([CH2:3][N:4]([CH3:1])[CH3:5])=[CH:28][N:29]=[C:25]3[CH:24]=[CH:23][CH:22]=2)[C:11]1=[O:30])[CH2:7][CH2:8][CH3:9]

참가 물질

6

반응물 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 569791215-Butylidene-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

생성물 1

HCID 570724355-Butylidene-3-[4-(3-dimethylaminomethylimidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

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온도
80 °C

실험 절차

To a solution of 0.27 ml (3.6 mmol) of formalin and 0.33 g (3.6 mmol) of a 50% aqueous dimethylamine solution in 20 ml of acetic acid, a solution of 1.13 g (3.0 mmol) of 5-butylidene-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione in 5 ml of acetic acid was added at 0° C., followed by stirring at 80° C. for 90 minutes. After cooling, the reaction mixture was poured into 50 ml of 50% aqueous sodium hydroxide under ice cooling conditions. The mixture was extracted with chloroform and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, chloroform/methanol=25/1) to yield 0.43 g (33.3%, yellow oily substance) of the desired product.

후처리

  1. temperatureAfter cooling
  2. extractionThe mixture was extracted with chloroform
  3. customdried
  4. distillationafter which the solvent was distilled off
  5. customThe residue was purified by column chromatography (eluent, chloroform/methanol=25/1)

출처 및 근거

ORD 기록
ord-fad4aecc3c424606b99c8356a387d768
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840732

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