Thionyl Chloride → HCID 59361875, compound

HRID 1808509Notes

Reaction equation

HRID 1808509 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[C:10]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=1)[NH:9][C:8]2=O)(=[O:3])[CH3:2].S(Cl)([Cl:29])=O>CN(C=O)C>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[C:10]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=1)[N:9]=[C:8]2[Cl:29])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1362032507-Methoxy-2-(3-nitrophenyl)-4-oxo-3,4-dihydroquinazolin-6-yl acetate

Product 1

HCID 59361875HCID 59361875, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the 7-methoxy-2-(3-nitrophenyl)-4-oxo-3,4-dihydroquinazolin-6-yl acetate (1.70 g, 4.79 mmol), thionyl chloride (30 mL) and anhydrous DMF (0.6 mL) were refluxed for 2.5 h. The volatiles were removed in vacuo and the residue dissolved in CH2CL2 (500 mL) and was washed with water, sat. NaHCO3, water and brine, dried (Na2SO4), filtered and concentrated in vacuo to 4-chloro-7-methoxy-2-(3-nitrophenyl)quinazolin-6-yl acetate. (1.6 g, 4.23 mmol, 88%). HPLC retention time 9.75 min.

Workup

  1. temperaturewere refluxed for 2.5 h
  2. customThe volatiles were removed in vacuo
  3. dissolutionthe residue dissolved in CH2CL2 (500 mL)
  4. washwas washed with water, sat. NaHCO3, water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to 4-chloro-7-methoxy-2-(3-nitrophenyl)quinazolin-6-yl acetate

Sources & evidence

ORD record
ord-f7529c27122c4479bf15ef888f998f21
Source dataset
uspto-grants-2013_01
Patent number
US08357693B2

Reaction notes

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