Thionyl Chloride → HCID 22030702, compound

HRID 2084024Notes

Reaction equation

HRID 2084024 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][N:17]([CH3:21])[CH2:16]1)[N:9]=[CH:8][NH:7][C:6]2=O.S(Cl)([Cl:25])=O>CN(C=O)C>[Cl:25][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:14][CH:15]3[CH2:20][CH2:19][CH2:18][N:17]([CH3:21])[CH2:16]3)=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 135763126HCID 135763126, compound

Product 1

HCID 22030702HCID 22030702, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-methoxy-7-(N-methylpiperidin-3-ylmethoxy)-3,4-dihydroquinazolin-4-one (2.72 g, 8.9 mmol), thionyl chloride (90 ml) and DMF (0.5 ml) was stirred and heated to reflux for 45 minutes. The mixture was evaporated and the residue was azeotroped with toluene. The residue was taken up in water and basified to pH8 by the addition of a saturated aqueous sodium hydrogen carbonate solution. The aqueous layer was extracted with ethyl acetate (4×400 ml). The combined organic extracts were washed in turn with a saturated aqueous sodium hydrogen carbonate solution, water and brine, dried (MgSO4) and evaporated. The residue was dried overnight at 40° C. under vacuum to give 4-chloro-6-methoxy-7-(N-methylpiperidin-3-ylmethoxy)quinazoline (2.62 g, 91%) as a solid; NMR: (DMSOd6) 1.1 (m, 1H), 1.42-1.96 (m, 5H), 2.09 (m, 1H), 2.15 (s, 3H), 2.6 (d, 1H), 2.8 (d, 1H), 3.98 (s, 3H), 4.1 (d, 2H), 7.35 (s, 1H), 7.42 (s, 1H), 8.84 (s, 1H); Mass: M+H+ 322.

Workup

  1. temperatureheated
  2. temperatureto reflux for 45 minutes
  3. customThe mixture was evaporated
  4. customthe residue was azeotroped with toluene
  5. additionThe residue was taken up in water and basified to pH8 by the addition of a saturated aqueous sodium hydrogen carbonate solution
  6. extractionThe aqueous layer was extracted with ethyl acetate (4×400 ml)
  7. washThe combined organic extracts were washed in turn with a saturated aqueous sodium hydrogen carbonate solution, water and brine
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customThe residue was dried overnight at 40° C. under vacuum

Sources & evidence

ORD record
ord-44b90fbcd90a4dfe94c2ac9981dc6391
Source dataset
uspto-grants-2004_04
Patent number
US06716847B2

Reaction notes

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