Water → 7-Nitro-4-methyl-4H-benzo[1,4]thiazin-3-one

HRID 1991288Notes

Reaction equation

HRID 1991288 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[NH:8][C:9](=[O:12])[CH2:10][S:11][C:6]=2[CH:5]=1)([O-:3])=[O:2].[C:15](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C>[CH3:15][N:8]1[C:7]2[CH:13]=[CH:14][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[S:11][CH2:10][C:9]1=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 3701217-Nitro-2H-benzo[b][1,4]thiazin-3(4H)-one

Product 1

HCID 218777807-Nitro-4-methyl-4H-benzo[1,4]thiazin-3-oneYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred suspension of 3,4-dihydro-7-nitro-2H-1,4-benzothiazin-3-one (Step 2, 4.7 g, 22.3 mmol) and potassium carbonate (3.70 g, 26.8 mmol) in dry DMF (40 mL) in an ice bath is added iodomethane (4.16 mL, 66.8 mmol). The reaction mixture is taken out of the ice bath and heated at 50° C. for 1-2 h. The resulting mixture is allowed to cool down. Water (35 mL) and ice are added and the precipitate is filtered off and washed with water (10 mL). The resulting solid is dried under high vacuum to give the title compound as a yellow solid (4.5 g, 90%), MS m/z 225.5 (M+H)+.

Workup

  1. temperatureto cool down
  2. filtrationthe precipitate is filtered off
  3. washwashed with water (10 mL)
  4. customThe resulting solid is dried under high vacuum

Sources & evidence

ORD record
ord-1bff3c2c22264bdb92ffa679ea71413f
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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