Methyl iodide → HCID 136403345, compound

HRID 1091041Notes

Reaction equation

HRID 1091041 reaction equation
[C:1]([NH:9][C:10]([NH:12][C:13]1[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=1[C:15]([NH:17][CH3:18])=[O:16])=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:25]I>CN(C)C=O.O>[C:1]([NH:9][C:10]([S:11][CH3:25])=[N:12][C:13]1[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=1[C:15]([NH:17][CH3:18])=[O:16])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 15135525HCID 15135525, compound

Product 1

HCID 136403345HCID 136403345, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 0.10 g of 2-[[(benzoylamino)thioxomethyl]amino]-N-methylbenzamide in 2.0 ml of N,N-dimethylformamide was added 0.35 ml of 1N sodium hydroxide at 0° C., followed by 0.04 ml of methyl iodide. The solution was stirred and allowed to reach room temperature over 30 minutes. This was diluted with water to give 0.074 g of N-benzoyl-N'-(2-methylaminocarbonylphenyl)carbamimidothioic acid, methyl ester as colorless crystals, mp 193°-195° C. This compound was reacted with sodium hydride in tetrahydrofuran by refluxing for 21/2 hours to give N-(3,4-dihydro-3-methyl-4-oxo-2-quinazolinyl)benzamide, mp 185°-187° C.

Sources & evidence

ORD record
ord-c3c53e66ce514856a1578de180e44e60
Source dataset
uspto-grants-1992_01
Patent number
US05084457

Reaction notes

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