Methyl iodide → 8-iodo-3-methyl-2-(methylthio)quinazolin-4(3H)-one

HRID 1055810Notes

Reaction equation

HRID 1055810 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[S:12])[N:8]([CH3:13])[C:7]2=[O:14].[C:15]([O-])([O-])=O.[K+].[K+].CI>C1COCC1>[I:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([S:12][CH3:15])[N:8]([CH3:13])[C:7]2=[O:14]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 897839658-Iodo-2-mercapto-3-methylquinazolin-4(3h)-one

Product 1

HCID 897822188-iodo-3-methyl-2-(methylthio)quinazolin-4(3H)-oneYield 97.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At RT, to a mixture of 8-iodo-3-methyl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one (11.2 g g, 35.3 mmol) and K2CO3 (9.76 g, 70.6 mmol) in THF (100 mL) was added MeI (6.58 mL, 106 mmol). The reaction was heated to reflux for 6 h, and then cooled to RT. The mixture was poured into ice/water (300 mL) and stirred for 10 min. The suspension was filtered and the solid was washed with cold water (20 mL) followed by cold ether (20 mL). The solid was dried to give 8-iodo-3-methyl-2-(methylthio)quinazolin-4(3H)-one (700a; 11.4 g, 97% yield) as an off-white solid. Crude material was used in the next step. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.31 (1H, dd, J=7.6, 1.4 Hz), 8.08 (1H, dd, J=7.8, 1.4 Hz), 7.19 (1H, t, J=7.7 Hz), 3.51 (3H, s), 2.73 (3H, s). m/z (ES, +ve) 332.9 (M+H)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 6 h
  3. filtrationThe suspension was filtered
  4. washthe solid was washed with cold water (20 mL)
  5. customThe solid was dried

Sources & evidence

ORD record
ord-1f912b41b29f4e118cc5be67042d0fc6
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

Loading…