Potassium Carbonate → 5-(3-(Hydroxymethyl)phenylthio)nicotinonitrile

HRID 2267050

반응식

HRID 2267050 반응식
C([O-])([O-])=O.[K+].[K+].[SH:7][C:8]1[CH:9]=[C:10]([CH2:14][OH:15])[CH:11]=[CH:12][CH:13]=1.Br[C:17]1[CH:18]=[N:19][CH:20]=[C:21]([CH:24]=1)[C:22]#[N:23]>CC(N(C)C)=O.CCOC(C)=O>[OH:15][CH2:14][C:10]1[CH:9]=[C:8]([S:7][C:17]2[CH:18]=[N:19][CH:20]=[C:21]([CH:24]=2)[C:22]#[N:23])[CH:13]=[CH:12][CH:11]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 7367935-BromonicotinonitrileHCID 12813879(3-Sulfanylphenyl)methanol

생성물 1

HCID 685380695-(3-(Hydroxymethyl)phenylthio)nicotinonitrile수율 99.1%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

반응 조건

온도
110 °C

실험 절차

Add K2CO3 (6.91 g, 50.0 mmol) to a solution of (3-mercaptophenyl)methanol (2.94 g, 21.0 mmol) and 5-bromonicotinonitrile (3.66 g, 20.0 mmol) in DMA (100 mL). Heat the mixture at 110° C. for 2 h. Cool to room temperature. Dilute with EtOAc. Filter. Wash the residue with EtOAc. Concentrate. Dissolve the residue in EtOAc and filter. Concentrate to afford the title compound (4.80 g, quant.): 1H NMR (CDCl3) δ 2.20 (t, J=5.5 Hz, 1H), 4.74 (d, J=5.5 Hz, 2H), 7.38-7.44 (m, 3H), 7.52-7.53 (m, 1H), 7.62 (dd, J=2.0, 2.3 Hz, 1H), 8.62 (dd, J=2.0, 2.3 Hz, 2H).

후처리

  1. temperatureCool to room temperature
  2. filtrationFilter
  3. washWash the residue with EtOAc
  4. concentrationConcentrate
  5. dissolutionDissolve the residue in EtOAc
  6. filtrationfilter
  7. concentrationConcentrate

출처 및 근거

ORD 기록
ord-e8cfe5cc54d54b198fb4510658f311ca
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858646B2

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