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

HRID 1108254Notes

Reaction equation

HRID 1108254 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a18dd21f10224723b4b5d23626b7d5a7
Source dataset
uspto-grants-2000_05
Patent number
US06066638

Reaction notes

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