Ammonia → HCID 86698307, compound

HRID 2408992Notes

Reaction equation

HRID 2408992 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][C:20]=2[O:21][CH3:22])[N:17]=[C:16]([CH3:23])[NH:15][C:14]3=O)[CH2:3][CH2:2]1.S(Cl)([Cl:27])=O.N>CN(C=O)C>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][C:20]=2[O:21][CH3:22])[N:17]=[C:16]([CH3:23])[N:15]=[C:14]3[Cl:27])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 136378638HCID 136378638, compound

Product 1

HCID 86698307HCID 86698307, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-(3-morpholinopropoxy)-7-methoxy-2-methylquinazolin-4(3H)-one (600 mg), thionyl chloride (20 mL) and DMF (0.5 mL) was refluxed for 3 h. The reaction mixture was attained to rt and poured into ice cold water and stirred for 10 min. The solution was basified with ammonia solution and extracted with chloroform (3×100 mL). 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 a yellow color solid (500 mg, 79%), mp 116-118° C. 1H NMR (400 MHz, CDCl3): δ 7.36 (1H, s), 7.25 (1H, s), 4.25 (2H, t, J=6.6 Hz), 4.03 (3H, s), 3.73 (4H, t, J=4.6 Hz), 2.79 (3H, s), 2.58 (2H, t, J=7.2 Hz), 2.49 (4H, t, J=4.4 Hz), 2.12 (2H, pentet, J=6.8 Hz); LC-MS (positive ion mode): m/z 352, 354 (M+H)±.

Workup

  1. temperaturewas refluxed for 3 h
  2. customwas attained to rt
  3. additionpoured into ice cold water
  4. extractionextracted with chloroform (3×100 mL)
  5. washThe combined CHCl3 layer was washed water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationThe solution was filtered
  8. customevaporated the solvent

Sources & evidence

ORD record
ord-1bfe3f5c0c874f1ca05cebfbe72f8f9e
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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