Methyl iodide → [3-(Benzylsulfanyl)phenyl]methylcyanamide

HRID 556759노트

반응식

HRID 556759 반응식
[CH2:1]([S:8][C:9]1[CH:10]=[C:11]([NH:15][C:16]#[N:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:18](N(C(C)C)CC)(C)C.CI>C(#N)C>[CH2:1]([S:8][C:9]1[CH:10]=[C:11]([N:15]([CH3:18])[C:16]#[N:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 59359635[3-(Benzylsulfanyl)phenyl]cyanamide

생성물 1

HCID 59359632[3-(Benzylsulfanyl)phenyl]methylcyanamide수율 80%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
82.5 °C

실험 절차

To a solution of 3-(benzylthio)phenylcyanamide (0.80 g, 3.33 mmol) dissolved in acetonitrile (8 mL) was added diisopropylethylamine (0.65 g, 5.0 mmol), followed by addition of methyl iodide (0.94 g, 6.66 mmol). The reaction mixture was refluxed at 80-85° C. for 3 hours. After removal of solvents the residue was taken by dichloromethane (40 ml) and the organic solution was washed by water (40 ml). After dried over MgSO4 and filtered, dichloromethane solution was then concentrated in vacuo to afford yellow oil as crude product. Purification by column chromatography (SiO2, Hexane/CH2Cl2, 50% to 100%) to afford 3-(benzylthio)phenyl-N-methylcyanamide as a pale yellow oil (0.67, 80% yield): CH2Cl2 Rf=0.45; 1H-NMR (CDCl3) δ (ppm) 7.3-6.8 (m, 9H, Ar—H), 4.06 (s, S—CH2, 2H), 3.57 (s, 3H, N—CH3).

후처리

  1. customAfter removal of solvents the residue
  2. washthe organic solution was washed by water (40 ml)
  3. dry with materialAfter dried over MgSO4
  4. filtrationfiltered
  5. concentrationdichloromethane solution was then concentrated in vacuo
  6. customto afford yellow oil as crude product
  7. customPurification by column chromatography (SiO2, Hexane/CH2Cl2, 50% to 100%)

출처 및 근거

ORD 기록
ord-cb1b9ed4654748c4ac8d0e5920d58402
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058311B2

반응 노트

불러오는 중…