Dimethylamine → N,N-dimethyl-[6-[4-(2-thenoyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-ylmethyl]amine

HRID 611301노트

반응식

HRID 611301 반응식
[C:1]1([C:6]([C:8]2[CH:24]=[CH:23][C:11]([C:12]([N:14]3[CH2:19][CH2:18][C:17]4[CH:20]=[CH:21][O:22][C:16]=4[CH2:15]3)=[O:13])=[CH:10][CH:9]=2)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1.[CH3:25][NH:26][CH3:27].[CH2:28]=O>C(O)(=O)C>[CH3:25][N:26]([CH2:28][C:21]1[O:22][C:16]2[CH2:15][N:14]([C:12](=[O:13])[C:11]3[CH:10]=[CH:9][C:8]([C:6](=[O:7])[C:1]4[S:5][CH:4]=[CH:3][CH:2]=4)=[CH:24][CH:23]=3)[CH2:19][CH2:18][C:17]=2[CH:20]=1)[CH3:27]

참가 물질

5

반응물 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 19600102HCID 19600102, 화합물

생성물 1

HCID 19599886N,N-dimethyl-[6-[4-(2-thenoyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-ylmethyl]amine

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
100 °C

실험 절차

To a solution of 0.251 g (0.744 mmol) of 6-[4-(2-thenoyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridine in 10 ml of acetic acid, 0.10 g (1.1 mmol) of 50% aqueous dimethylamine and 0.09 g (1.1 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 0.5 hours. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with an aqueous sodium hydroxide and extracted with ethyl acetate 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1) to yield the desired product.

후처리

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. extractionextracted with ethyl acetate 3 times
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1)

출처 및 근거

ORD 기록
ord-5de31371bdc6443c855ede361b009347
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998433

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