Methyl isothiocyanate → 8-Iodo-2-mercapto-3-methylquinazolin-4(3h)-one
Reaction equation
[NH2:1][C:2]1[C:10]([I:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[CH3:12][N:13]=[C:14]=[S:15]>CCO>[I:11][C:10]1[CH:9]=[CH:8][CH:7]=[C:3]2[C:2]=1[NH:1][C:14](=[S:15])[N:13]([CH3:12])[C:4]2=[O:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A sealable flask was charged with 2-amino-3-iodobenzoic acid (Bosche Scientific; 10 g, 38.0 mmol) and methyl isothiocyanate (5.56 g, 76 mmol) in EtOH (120 mL) followed by TEA (7.93 mL, 57.0 mmol). The flask was sealed and heated in an oil bath at 100° C. for 4 h with a blast shield. The mixture was cooled to RT and the solvent was removed in vacuo. The residue was triturated with Et2O (40 mL) and filtered, dried to give 8-iodo-3-methyl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one (11.22 g, 35.3 mmol, 93% yield) as an off white solid. Crude material was used in the next step. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.97 (1H, br.), 8.23 (1H, d, J=8.4 Hz), 8.00 (1H, d, J=8.0 Hz), 7.15 (1H, t, J=7.5 Hz), 3.65 (3H, s).). m/z (ES, +ve) 318.8 (M+H)+.
Workup
- customThe flask was sealed
- temperatureThe mixture was cooled to RT
- customthe solvent was removed in vacuo
- customThe residue was triturated with Et2O (40 mL)
- filtrationfiltered
- customdried
Sources & evidence
- ORD record
- ord-0196706eaa6049dca3c50d6e0052557a
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394297B2
Reaction notes
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