Chloroacetonitrile → methyl 2-(chloromethyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylate

HRID 1616119Notes

Reaction equation

HRID 1616119 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.[Cl:16][CH2:17][C:18]#[N:19]>Cl.O1CCOCC1>[Cl:16][CH2:17][C:18]1[NH:19][C:4](=[O:6])[C:3]2[C:2](=[CH:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=2)[N:1]=1

Participants

5

Reactant 2

HCID 7856ChloroacetonitrileHCID 79336Dimethyl aminoterephthalate

Product 1

HCID 135520070methyl 2-(chloromethyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylateYield 88%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of dimethyl 2-aminoterephthalate (1.70 g, 8.1 mmol) in 4.0 M hydrochloric acid in 1,4-dioxane (20 mL) was added chloroacetonitrile (0.88 mL, 14 mmol). The reaction mixture was heated to 50° C. and stirred for 3 h. The mixture was then cooled to rt, concentrated and the residue was twice co-evaporated with toluene. Water was added and the solid was filtered to afford methyl 2-(chloromethyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylate (1.8 g, 88%). LC-MS: (FA) ES+ 253; 1H NMR (400 MHz, DMSO) δ 12.81 (s, 1H), 8.23 (d, J=8.2 Hz, 1H), 8.14 (d, J=1.1 Hz, 1H), 8.02 (dd, J=8.2, 1.6 Hz, 1H), 4.57 (s, 2H), 3.92 (s, 3H).

Workup

  1. temperatureThe mixture was then cooled to rt
  2. concentrationconcentrated
  3. additionWater was added
  4. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-eddfddb33d4a4b55a1af9ddc39c27b3a
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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