3-Hydroxypicolinamide → 3-Hydroxythiopicolinamide

HRID 53572

반응식

HRID 53572 반응식
[OH:1][C:2]1[C:3]([C:8]([NH2:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:20])=CC=1>C(Cl)CCl.CCOC(C)=O>[OH:1][C:2]1[C:3]([C:8](=[S:20])[NH2:10])=[N:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 702773-HydroxypicolinamideHCID 87949Lawesson's reagent

생성물 1

HCID 1360468883-Hydroxythiopicolinamide수율 69.1%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 8857Ethyl Acetate용매

실험 절차

A stirred solution of 3-hydroxypicolinamide (1.35 g, 9.75 mmol) and Lawesson's reagent (2.37 g, 5.85 mmol) in dry ClCH2CH2Cl (12 mL) was heated to reflux under nitrogen for 5 hr. At ambient temperature, he mixture was diluted with EtOAc (50 mL), washed with half-saturated aq. NaCl (30 mL) containing NaHCO3 (840 mg) and with brine (20 mL). After drying over MgSO4 and filtration, the filtrate was concentrated in vacuo to give a brown solid, which was subject to flash chromatography on silica gel (CH2Cl2 as eluent) to provide 3c (623 mg, 42%) as a greenish yellow solid after crystallization from EtOAc/hexane. mp 152.0°-153.0° C.; IR (KBr) 3372, 3259, 2464, 1626, 1458, 1317 cm-1 ; 1HNMR (DMSO-d6) δ7.33 (1H, dd, J=8.6 and 1.0 Hz, Ar), 7.46 (1H, dd, J=8.6 and 4.3 Hz, Ar), 8.07-8.10 (1H, m, Ar), 8.15(1H, s, NH), 8.49 (1H, s, NH), 12.76 (1H, s, OH); FABMS m/z 154 (M+); Anal. Calcd for C6H6N2OS: C, 46.74; H, 3.92; N, 18.17. Found: C, 46.83H, 3.89; N, 17.90.

후처리

  1. temperatureto reflux under nitrogen for 5 hr
  2. washwashed with half-saturated aq. NaCl (30 mL)
  3. additioncontaining NaHCO3 (840 mg)
  4. dry with materialAfter drying over MgSO4 and filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customto give a brown solid, which

출처 및 근거

ORD 기록
ord-36fe0e566cb94948a580db7481925ac7
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620968

연결된 노트

불러오는 중…