Potassium Carbonate → 7-Nitro-2H-benzo[b][1,4]thiazin-3(4H)-one

HRID 896151Notes

Reaction equation

HRID 896151 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[SH:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20](OC)=[O:21]>CN(C=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:20](=[O:21])[CH2:19][S:11][C:3]=2[CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 109866912-Amino-5-nitrobenzenethiol

Product 1

HCID 3701217-Nitro-2H-benzo[b][1,4]thiazin-3(4H)-oneYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred suspension of 2-amino-5-nitrobenzenethiol (Step 1, 29 g, 139.8 mmol) and potassium carbonate (115.93 g, 838.8 mmol) in dry DMF (150 mL) is added methyl bromoacetate (15.88 mL, 167.8 mmol). The reaction mixture is heated at 50° C. for 16 h at which time the reaction is quenched with ice and water (50 mL). The precipitate is filtered and dried under high vacuum to give the title compound as a yellow solid (21.69 g, 74%), MS m/z 211.5 (M+H)+.

Workup

  1. customis quenched with ice and water (50 mL)
  2. filtrationThe precipitate is filtered
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-20c8a6a9b8ed422f98ce6f07a9c2478e
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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