Dimethyl aminoterephthalate → HCID 136390988, compound

HRID 1616136Notes

Reaction equation

HRID 1616136 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.[C:16]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])#[N:17]>Cl.O1CCOCC1>[O:6]=[C:4]1[C:3]2[C:2](=[CH:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=2)[N:1]=[C:16]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[NH:17]1

Participants

5

Reactant 2

HCID 79336Dimethyl aminoterephthalateHCID 79660Benzyl cyanoformate

Product 1

HCID 136390988HCID 136390988, compoundYield 98.5%

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 benzyl cyanoformate (2.0 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. Diethyl ether was added and the solid was filtered to afford 2-benzyl 7-methyl 4-oxo-3,4-dihydroquinazoline-2,7-dicarboxylate (2.7 g, 98%). LC-MS: (FA) ES+ 339.

Workup

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

Sources & evidence

ORD record
ord-f5f3975d30674f7f83d985062fdb6fac
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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