Potassium Carbonate → 6,8-diiodo-2-(propylthio)-3-[(tetrahydro-2-furanyl)methyl]-4(3H)-quinazolinone

HRID 1108254노트

반응식

HRID 1108254 반응식
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([I:12])[CH:11]=1)[NH:8][C:7](=[S:13])[N:6]([CH2:14][CH:15]1[CH2:19][CH2:18][CH2:17][O:16]1)[C:5]2=[O:20].[CH2:21](I)[CH2:22][CH3:23].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([I:12])[CH:11]=1)[N:8]=[C:7]([S:13][CH2:21][CH2:22][CH3:23])[N:6]([CH2:14][CH:15]1[CH2:19][CH2:18][CH2:17][O:16]1)[C:5]2=[O:20]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 18784610HCID 18784610, 화합물

생성물 1

HCID 211962736,8-diiodo-2-(propylthio)-3-[(tetrahydro-2-furanyl)methyl]-4(3H)-quinazolinone수율 88.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of the title compound of Step A (0.86 g, 1.67 mmol), n-propyl iodide (0.85 g, 5.02 mmol) and potassium carbonate (2.3 g, 16.7 mmol) was stirred in dimethylformamide (20 mL) at ambient temperature for approximately 4 h. The reaction mixture was then concentrated to dryness in vacuo and partitioned between 200 mL each of ethyl acetate and water. The organic phase was then separated, washed with saturated aqueous NaCl, and dried over Na2SO4. Concentration in vacuo provided 0.82 g of the title compound of Step B, a compound of the invention, as a solid melting at 108-111° C. 1H NMR (300 MHz, CDCl3): δ 1.10 (t,3H), 1.63-1.80 (m,1H), 1.80-2.14 (m,5H), 3.24-3.45 (m,2H), 3.70-3.80 (m,1H), 3.90-4.00 (m,1H), 4.10-4.21 (m,2H), 4.35-4.47 (m,1H), 8.44 (d,1H), 8.48 (d,1H).

후처리

  1. concentrationThe reaction mixture was then concentrated to dryness in vacuo
  2. custompartitioned between 200 mL each of ethyl acetate and water
  3. customThe organic phase was then separated
  4. washwashed with saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationConcentration in vacuo

출처 및 근거

ORD 기록
ord-a18dd21f10224723b4b5d23626b7d5a7
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06066638

반응 노트

불러오는 중…