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4-Methoxy-alpha-toluenethiol → Methyl 3-[[(4-methoxyphenyl)methyl]thio]-2-pyridinecarboxylate

HRID 1084745
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HRID 1084745 반응식
CNN(NC)[C:4]([S:6][C:7]1[C:8]([C:13]([O:15][CH3:16])=[O:14])=[N:9][CH:10]=[CH:11][CH:12]=1)=O.CO.C[O-].[Na+].[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29](CS)=[CH:28][CH:27]=1>CO>[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:4][S:6][C:7]2[C:8]([C:13]([O:15][CH3:16])=[O:14])=[N:9][CH:10]=[CH:11][CH:12]=2)=[CH:28][CH:27]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 804074-Methoxy-alpha-toluenethiolHCID 23694274Sodium methanolate methanolHCID 86742402methyl 3-(N,N-dimethylaminocarbamoylthio)pyridine-2-carboxylate

생성물 1

HCID 14277622Methyl 3-[[(4-methoxyphenyl)methyl]thio]-2-pyridinecarboxylate수율 62.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 1.20 g (5 mmol) of methyl 3-(N,N-dimethylaminocarbamoylthio)pyridine-2-carboxylate in 5 mL of methanol and 1.5 mL (6 mmol) of 4.lM sodium methoxide methanol was stirred at room temperature for 10 minutes. Then the solvent was concentrated and the residue was dissolved in 5 mL of N,N-dimethylformamide and 5 mL of tetrahydrofuran. 0.936 g (6 mmol) of p-methoxybenzylmercaptan was added and the solution was stirred at room temperature for 18 hours. The solution was partitioned between ether and water and the aqueous layer was extracted with two portions of ether. The combined extracts were washed with brine, dried and concentrated. Recrystallization from methanol afforded 0.90 g (62%) of pale tan needles, m.p. 99°-100° C.

후처리

  1. concentrationThen the solvent was concentrated
  2. dissolutionthe residue was dissolved in 5 mL of N,N-dimethylformamide
  3. customThe solution was partitioned between ether and water
  4. extractionthe aqueous layer was extracted with two portions of ether
  5. washThe combined extracts were washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customRecrystallization from methanol

출처 및 근거

ORD 기록
ord-471ca076e5854011bd88dfe4edb17758
출처 데이터셋
uspto-grants-1991_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05006532

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