Acetic Anhydride → HCID 60703790, compound

HRID 1754979Notes

Reaction equation

HRID 1754979 reaction equation
O1[C:6](=[O:7])[CH2:5][O:4][CH2:3][C:2]1=[O:8].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:11]=1[CH3:17].C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+]>C(OC)(C)(C)C.O>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:2](=[O:8])[CH2:3][O:4][CH2:5][C:6]2=[O:7])=[CH:12][C:11]=1[CH3:17]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 233594-Bromo-3-methylanilineHCID 782321,4-Dioxane-2,6-dioneHCID 517045Sodium Acetate

Product 1

HCID 60703790HCID 60703790, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

[1,4]Dioxane-2,6-dione (312 mg, 2.69 mmol) was added to a solution of 4-bromo-3-methyl-phenylamine (500 mg, 2.69 mmol) in tBuOMe (7.0 ml), and the mixture was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure. Acetic anhydride (4.0 ml, 42.3 mmol) and sodium acetate (35 mg, 0.427 mmol) were added to the resulting residue, and the mixture was heated with stirring at 60° C. for three hours. Water was added to the reaction solution, and collection by filtration and trituration with water gave 4-(4-bromo-3-methyl-phenyl)-morpholine-3,5-dione (577 mg, 73%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. temperaturethe mixture was heated
  3. stirringwith stirring at 60° C. for three hours

Sources & evidence

ORD record
ord-2e292c38aca2476fb121fe75b397e03b
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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