Dimethylformamide → 4-Chloro-2-(3-nitrophenyl)quinazolin-6-yl acetate

HRID 61632Notes

Reaction equation

HRID 61632 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1)[NH:9][C:8]2=O)(=[O:3])[CH3:2].CN(C=O)C.O=S(Cl)[Cl:32]>>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1)[N:9]=[C:8]2[Cl:32])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 135796464HCID 135796464, compound

Product 1

HCID 569494764-Chloro-2-(3-nitrophenyl)quinazolin-6-yl acetate

Procedure

A suspension of 2-(3-nitrophenyl)-4-oxo-3,4-dihydroquinazolin-6-yl acetate (3.30 g, 10.1 mmol) in SOCl2 (65 mL) was added DMF (2 mL). The mixture was refluxed for 2.5 h, upon which the volatiles were removed in vacuo. The residue was taken up in CHCl3 (450 mL) and washed with sat NaHCO3 (200 ml) and water (200 mL). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo to give the product 4-chloro-2-(3-nitrophenyl)quinazolin-6-yl acetate (3.53 g, 10.3 mmol). HPLC retention time 9.748 min.

Workup

  1. temperatureThe mixture was refluxed for 2.5 h, upon which the volatiles
  2. customwere removed in vacuo
  3. washwashed
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-200ee9324b0148a7b446286d1025a863
Source dataset
uspto-grants-2016_09
Patent number
US09440961B2

Reaction notes

Loading…