Acetic Acid → 2-Iodo-4-oxo-4,5-dihydro-thieno[3,2-c]pyridine-7-carbonitrile

HRID 1268840노트

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HRID 1268840 반응식
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[C:5]([C:11]#[N:12])=[CH:4][NH:3]1.C(O)(=O)C.[I:17]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>O.CN(C=O)C>[I:17][C:9]1[S:10][C:6]2[C:5]([C:11]#[N:12])=[CH:4][NH:3][C:2](=[O:1])[C:7]=2[CH:8]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 184465784-Oxo-4,5-dihydrothieno[3,2-c]pyridine-7-carbonitrile

생성물 1

HCID 184465252-Iodo-4-oxo-4,5-dihydro-thieno[3,2-c]pyridine-7-carbonitrile수율 84.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

To 4-oxo-4,5-dihydro-thieno[3,2-c]pyridine-7-carbonitrile 24 (5 g, 28.4 mmol) in a 1:1 solution of acetic acid and DMF (18.4 mL) was added N-iodosuccinimide (12.8 g, 56.8 mmol). The reaction was warmed to 80° C. and stirred for 21 h. The reaction was diluted 10 fold with water and neutralized with aqueous sodium bicarbonate. The precipitate was filtered, washed with water and dried to provide 7.27 g of 25. 1H NMR (400 MHz, d6-DMSO) δ 12.45 (s, 1H), 8.25 (d, J=5 Hz, 1H), 7.77 (s, 1H).

후처리

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried

출처 및 근거

ORD 기록
ord-8d057555eb474f40a9b06e737b4f2896
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199119B2

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