Water → 2H-3,1-Benzoxazine-2,4(1H)-dione, 6-chloro-1-methyl-

HRID 884994Notes

Reaction equation

HRID 884994 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]2[NH:6][C:7](=[O:11])[O:8][C:9](=[O:10])[C:4]=2[CH:3]=1.[C:14](=O)([O-])[O-].[Na+].[Na+].CI.O>CN(C)C=O>[Cl:1][C:2]1[CH:13]=[CH:12][C:5]2[N:6]([CH3:14])[C:7](=[O:11])[O:8][C:9](=[O:10])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 784805-Chloroisatoic anhydride

Product 1

HCID 267242H-3,1-Benzoxazine-2,4(1H)-dione, 6-chloro-1-methyl-Yield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Chloro-1Hbenzo[d][1,3]oxazine-2,4-dione (22.88 g, 116 mmol) was dissolved in dimethylformamide (150 mL), and sodium carbonate (14.73 g, 139 mmol) was added. Methyl iodide (10.86 mL, 174 mmol) was then added dropwise. The reaction was stirred at room temperature overnight. Water (150 mL) was then added, and the mixture was stirred for 1 hour. The solid was collected by filtration. The impure solid was sonicated in methyl-tert-butyl ether for several minutes, and then collected by filtration yielding the product as a white solid (19.38 g, 79%). 1H NMR (300 MHz, DMSO-d6) δ 3.45 (s, 3H), 7.47 (d, 1H), 7.89 (dd, 1H), 7.94 (d, 1H).

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. filtrationThe solid was collected by filtration
  3. customThe impure solid was sonicated in methyl-tert-butyl ether for several minutes
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-fffb63438a0c4d9fa42d30209f24b88b
Source dataset
uspto-grants-2012_08
Patent number
US08242109B2

Reaction notes

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