Phosphorus oxychloride → HCID 67282899, compound

HRID 1616134Notes

Reaction equation

HRID 1616134 reaction equation
[CH2:1]([N:8]1[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)[NH:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:26])=O.C(N(CC)C(C)C)(C)C>>[CH2:1]([N:8]1[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]=[C:9]1[Cl:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 32253024HCID 32253024, compound

Product 1

HCID 67282899HCID 67282899, compoundYield 95.1%

Conditions

Temperature
120 °C

Procedure

Into a round bottom flask was added methyl 3-benzyl-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate (1.0 g, 3.2 mmol) dissolved in phosphoryl chloride (15.0 mL, 161 mmol) and N,N-diisopropylethylamine (1.2 mL, 7.1 mmol). The reaction mixture was heated to 120° C. and stirred for 2 d. 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 3-benzyl-2-chloro-4-oxo-3,4-dihydroquinazoline-7-carboxylate (1.0 g, 94%). LC-MS: (FA) ES+ 329.

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-af03a0fe4fbf4018b31e03386bfb2c15
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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