Water → 2,1,3-Benzothiadiazole, 4-methyl-5-nitro-

HRID 2378478Notes

Reaction equation

HRID 2378478 reaction equation
[CH3:1][C:2]1[C:7]2=[N:8][S:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[N+:11]([O-:14])([OH:13])=[O:12].OS(O)(=O)=O.O>OS(O)(=O)=O>[CH3:1][C:2]1[C:7]2=[N:8][S:9][N:10]=[C:6]2[CH:5]=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH3:1][C:2]1[C:7]2=[N:8][S:9][N:10]=[C:6]2[C:5]([N+:11]([O-:14])=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 27812624-Methyl-2,1,3-benzothiadiazoleHCID 71777668Sulfuric acid, mixt. with nitric acid

Product 2

HCID 6764462,1,3-Benzothiadiazole, 4-methyl-5-nitro-HCID 6764474-Methyl-7-nitrobenzo[1,2,5]thiadiazole

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-methyl-benzo[1,2,5]thiadiazole (5.57 g, 37.1 mmol) in conc. H2SO4 (14.5 mL) at 0° C. was slowly added HNO3/H2SO4 (3.25 mL/4.25 mL). The reaction mixture was stirred at 0° C. for 20 min and then at rt for 30 min and then was poured into iced water (200 mL). The resulting precipitate was isolated by filtration, rinsed with water and purified by silica gel flash chromatography, eluting with CHCl3 to give compound 839B (1.5 g) as a yellow solid and 4-methyl-7-nitrobenzo[1,2,5]thiadiazole (2.0 g) as a yellow solid.

Workup

  1. customat 0° C.
  2. waitat rt for 30 min
  3. customThe resulting precipitate was isolated by filtration
  4. washrinsed with water
  5. custompurified by silica gel flash chromatography
  6. washeluting with CHCl3

Sources & evidence

ORD record
ord-d3d87425689848c69e5cf503f6c171bb
Source dataset
uspto-grants-2008_12
Patent number
US07470797B2

Reaction notes

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