Phosphorus oxychloride → HCID 86698309, compound

HRID 2408994Notes

Reaction equation

HRID 2408994 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[NH:14][C:13](=O)[C:12]2[C:7](=[CH:8][C:9]([O:18][CH3:19])=[C:10]([O:16][CH3:17])[CH:11]=2)[N:6]=1)[CH3:3].P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:13]1[C:12]2[C:7](=[CH:8][C:9]([O:18][CH3:19])=[C:10]([O:16][CH3:17])[CH:11]=2)[N:6]=[C:5]([CH2:4][N:2]([CH3:3])[CH3:1])[N:14]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136378639HCID 136378639, compound

Product 1

HCID 86698309HCID 86698309, compoundYield 93%

Procedure

A mixture of 2-((dimethylamino)methyl)-6,7-dimethoxyquinazolin-4-(3H)-one (100 mg) and phosphorous oxychloride (10 mL) was refluxed for 2 h. Excess of POCl3 was evaporated under vacuum and the reaction mixture was attained to rt. The mixture was poured into ice cold water and basified with aqueous ammonia solution. The solution was extracted with chloroform (3×100 mL) and the combined CHCl3 layer was washed water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent to give the product as an off-white color solid (100 mg, 93%), mp 78-80° C. 1H NMR (400 MHz, CDCl3): δ 7.41 (1H, s), 7.38 (1H, s), 4.05 (6H, s), 3.82 (2H, s), 2.42 (6H, s); LC-MS (positive ion mode): m/z 282, 284 (M+H)+.

Workup

  1. temperaturewas refluxed for 2 h
  2. customExcess of POCl3 was evaporated under vacuum
  3. customwas attained to rt
  4. additionThe mixture was poured into ice cold water and basified with aqueous ammonia solution
  5. extractionThe solution was extracted with chloroform (3×100 mL)
  6. washthe combined CHCl3 layer was washed water, brine
  7. dry with materialdried over sodium sulfate
  8. filtrationThe solution was filtered
  9. customevaporated the solvent

Sources & evidence

ORD record
ord-c8599f16ecb8485b946e7c0f1555d530
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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