Methyl iodide → HCID 21535587, compound

HRID 1076973Notes

Reaction equation

HRID 1076973 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:22]=[CH:21][C:7]([CH2:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[N:11]=[C:10]2[NH2:20])=[CH:6][CH:5]=1.[CH3:23]I>CC(N(C)C)=O>[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[N:11]([CH3:23])[C:10]2=[NH:20])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12223348HCID 12223348, compound

Product 1

HCID 21535587HCID 21535587, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a mixture of 570 mg. of sodium hydride in 50.0 ml. of dimethylacetamide is added 2.7 g. of 1-(4'-fluorobenzyl)-2-amino-quinazolin-4(1H)-one followed by stirring for one hour at room temperature. There is then added 3.0 g. of methyl iodide and the resulting solution is stirred for 18 hours at room temperature. The resulting mixture is then evaporated in vacuo to remove the solvent and the residue stripped twice with benzene. The resulting residue is poured over ice-water and the precipitate which forms (about 0.5 hour) is washed with water, dried by suction, dissolved in methylene chloride, treated with sodium sulfate, alumina and charcoal and then filtered through Celite. The solvent is exchanged for ether and concentration results in a precipitate which is recovered by filtering, washed with pentane and dried under reduced pressure to obtain 1-(4'-fluorobenzyl)-2-imino-3-methyl-2,3-dihydro-quinazolin-4(1H)-one, m.p. 135°-137°C.

Workup

  1. additionTo a mixture of 570 mg
  2. additionThere is then added 3.0 g
  3. customThe resulting mixture is then evaporated in vacuo
  4. customto remove the solvent
  5. additionThe resulting residue is poured over ice-water
  6. custom(about 0.5 hour)
  7. washis washed with water
  8. customdried by suction
  9. dissolutiondissolved in methylene chloride
  10. additiontreated with sodium sulfate, alumina and charcoal
  11. filtrationfiltered through Celite
  12. concentrationThe solvent is exchanged for ether and concentration
  13. customresults in a precipitate which
  14. customis recovered
  15. filtrationby filtering
  16. washwashed with pentane
  17. customdried under reduced pressure

Sources & evidence

ORD record
ord-428f9fb27b2e450e8a6d9d82fab28cd4
Source dataset
uspto-grants-1976_05
Patent number
US03959279

Reaction notes

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