Methyl iodide → Methyl 2-(3-methoxybenzylthio)nicotinate

HRID 1200004

반응식

HRID 1200004 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[CH2:6][S:7][C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].[CH3:20]I>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[CH2:6][S:7][C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([O:12][CH3:20])=[O:11]

참가 물질

4

반응물 2

HCID 6328Methyl iodideHCID 8593402-(3-Methoxybenzylthio)nicotinic acid

생성물 1

HCID 14277645Methyl 2-(3-methoxybenzylthio)nicotinate수율 92%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A suspension of 7.15 g (0.026 mole) of 2-(3-methoxybenzylthio)nicotinic acid in 75 ml of dry acetonitrile was treated with 3.95 g (0.026 mole) of 1,8-diazabicyclo[5,4,0]-under-7-ene (DBU). A solution formed and 4.26 g (0.030 mole) of methyl iodide was added over one minute. After keeping the reaction mixture at room temperature for 24 hours, the solution was evaporated in vacuo. The residue was partitioned between 100 ml of ether and 50 ml of water. The ether layer was washed with 50 ml of H2O, dried, and evaporated to a small volume. The addition of hexane with cooling yielded 6.9 g (92% of theory) of methyl 2-(3-methoxybenzylthio)nicotinate; m.p. 69°-70° C.

후처리

  1. customA solution formed
  2. customat room temperature
  3. customfor 24 hours
  4. customthe solution was evaporated in vacuo
  5. customThe residue was partitioned between 100 ml of ether and 50 ml of water
  6. washThe ether layer was washed with 50 ml of H2O
  7. customdried
  8. customevaporated to a small volume
  9. additionThe addition of hexane
  10. temperaturewith cooling

출처 및 근거

ORD 기록
ord-4c7eadf0d4634414b90c69607db25147
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04904672

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