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

HRID 723876Notes

Reaction equation

HRID 723876 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-f77ec6357c294962af3153e245634f0a
Source dataset
uspto-grants-2006_11
Patent number
US07141588B2

Reaction notes

Loading…