Dimethylformamide → HCID 58306551, compound

HRID 1909853Notes

Reaction equation

HRID 1909853 reaction equation
[NH:1]1[C:6]2[S:7][C:8]3[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=3[C:5]=2[C:4](=[O:14])[O:3][C:2]1=[O:15].[C:16](=O)([O-])[O-].[K+].[K+].CN(C=O)C.CI>O>[CH3:16][N:1]1[C:6]2[S:7][C:8]3[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=3[C:5]=2[C:4](=[O:14])[O:3][C:2]1=[O:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 10656703HCID 10656703, compound

Product 1

HCID 58306551HCID 58306551, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5,6,7,8-tetrahydro-2H-[1]benzothieno[2,3-d][1,3]oxazine-2,4(1H)-dione (1.5 g) and potassium carbonate (1.4 g) was added DMF (15 mL), and methyl iodide (1.2 m) was added thereto under ice-cooling, followed by stirring at room temperature for 6 hours. Methyl iodide (0.61 mL) was added thereto, followed by stirring at room temperature overnight, water (15 mL) was added to the reaction mixture, and the solid was collected by filtration, washed with water, and dried under reduced pressure to obtain 1-methyl-5,6,7,8-tetrahydro-2H-[1]benzothieno[2,3-d][1,3]oxazine-2,4(1H)-dione (1.3 g).

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. stirringby stirring at room temperature overnight
  4. filtrationthe solid was collected by filtration
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-d5955fa0b9c743148b805b2b29ecb979
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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