Ethyl Acetoacetate → HCID 66747120, compound

HRID 1466990Notes

Reaction equation

[CH3:1][C:2]1C2C(=O)OC(=O)[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.O=[C:15]([CH3:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].[OH-].[Na+].O=P(Cl)(Cl)[Cl:27].O1[CH2:35][CH2:34]OCC1>>[Cl:27][C:15]1[C:22]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[CH3:1])[N:7]=[C:34]([CH3:35])[C:16]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

Reactant 5

HCID 8868Ethyl Acetoacetate

HCID 14798Sodium Hydroxide

HCID 24813Phosphorus oxychloride

HCID 312751,4-Dioxane

HCID 104875225-methyl-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 66747120HCID 66747120, compound

Procedure

A solution of 5-methyl-1H-benzo[d][1,3]oxazine-2,4-dione (Example 12c) (1.36 g, 7.68 mmol), ethyl 3-oxobutanoate (1.46 mL, 11.5 mmol), and NaOH (0.046 g, 1.15 mmol) in anhydrous dioxane (10 mL) were refluxed under nitrogen for 15 hrs. The solvent was then removed under vacuum, and the residue was re-dissolved in DMF (15 mL). To this solution was added POCl3 (1.41 mL, 15.4 mmol), and the reaction mixture was stirred at room temperature for 45 minutes.

Workup

customThe solvent was then removed under vacuum
dissolutionthe residue was re-dissolved in DMF (15 mL)

Sources & evidence

ORD record: ord-75aeadb63a5a4c2b8239a9147ecf9a97
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000054B2

Reaction notes

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