Phosphorus oxychloride → HCID 67283428, compound

HRID 1616131Notes

Reaction equation

HRID 1616131 reaction equation
O=[C:2]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10](=[O:18])[C:9]2[C:4](=[CH:5][C:6]([C:19]([O:21][CH3:22])=[O:20])=[CH:7][CH:8]=2)[NH:3]1.P(Cl)(Cl)([Cl:25])=O.C(N(CC)C(C)C)(C)C>>[Cl:25][C:2]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10](=[O:18])[C:9]2[C:4](=[CH:5][C:6]([C:19]([O:21][CH3:22])=[O:20])=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 944357HCID 944357, compound

Product 1

HCID 67283428HCID 67283428, compoundYield 77.2%

Conditions

Temperature
120 °C

Procedure

Into a round bottom flask was added methyl 2,4-dioxo-3-phenyl-1,2,3,4-tetrahydroquinazoline-7-carboxylate (0.21 g, 0.70 mmol) dissolved in phosphoryl chloride (3.0 mL, 32.2 mmol) and N,N-diisopropylethylamine (0.27 mL, 1.6 mmol). The reaction mixture was heated to 120° C. and stirred overnight. The mixture was then cooled to rt and concentrated. The residue was poured over ice and the resulting solid was filtered and washed with water to afford methyl 2-chloro-4-oxo-3-phenyl-3,4-dihydroquinazoline-7-carboxylate (0.17 g, 77%). LC-MS: (FA) ES+ 315.

Workup

  1. temperatureThe mixture was then cooled to rt
  2. concentrationconcentrated
  3. additionThe residue was poured over ice
  4. filtrationthe resulting solid was filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-ecbd4aaf6b4b410cba63581705dce060
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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