Phosphorus oxychloride → HCID 67283727, compound

HRID 1616128Notes

Reaction equation

HRID 1616128 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13]([C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:15]=3)[NH:10][C:9]2=O)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:26])=O.C(N(CC)C(C)C)(C)C>>[Cl:26][C:9]1[N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:15]=2)[N:10]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 67282653HCID 67282653, compound

Product 1

HCID 67283727HCID 67283727, compoundYield 98%

Conditions

Temperature
120 °C

Procedure

Into a round bottom flask was added methyl 3-(4-chlorophenyl)-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate (0.28 g, 0.76 mmol) dissolved in phosphoryl chloride (3.2 mL, 34.5 mmol) and N,N-diisopropylethylamine (0.29 mL, 1.7 mmol). The reaction mixture was heated to 120° C. and stirred for 5 h. 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-3-(4-chlorophenyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylate (0.26 g, 98%). LC-MS: (FA) ES+ 350.

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-7cdb213622924aceb5e345715aa84185
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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