Dimethyl Sulfate → 5-Chloro-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 1155519Notes

Reaction equation

HRID 1155519 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:13]2[C:14](=[O:19])[O:15][C:16](=[O:18])[NH:17][C:12]=2[CH:11]=[CH:10][CH:9]=1.S(OC)(OC)(=O)=O>CS(C)=O>[CH3:1][N:17]1[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([Cl:7])[C:13]=2[C:14](=[O:19])[O:15][C:16]1=[O:18]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 6390585-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 5867555-Chloro-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Anhydrous potassium carbonate (16.8 g.) was added gradually to a suspension of the known compound 1,2-dihydro-5-chloro-2,4-dioxo-3,1-(4H)-benzoxazine (11.7 g.) in dry dimethyl sulphoxide (110 ml.) and the mixture stirred at room temperature for 20 minutes Dimethyl sulphate (7 ml.) was added dropwise with vigorous stirring at 30°-35° for 12 minutes and the mixture allowed to settle. The supernatant liquid was decanted into an ice/dilute hydrochloric acid mixture (600 ml.; 0.05 M.HCl). The resulting precipitate was collected, washed with water and dried in vacuo to give 1,2-dihydro-1-methyl-5-chloro-2,4-dioxo-3,1-(4H)-benzoxazine m.p. 199°-201° (dec.).

Workup

  1. additionwas added dropwise
  2. customThe supernatant liquid was decanted into an ice/dilute hydrochloric acid mixture (600 ml.; 0.05 M.HCl)
  3. customThe resulting precipitate was collected
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-2bb0bfe0881f49bfb360c786e310241a
Source dataset
uspto-grants-1981_11
Patent number
US04302460

Reaction notes

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