Acetic Acid → 4-Methyl-2,1,3-benzothiadiazol-5-amine

HRID 2378479Notes

Reaction equation

HRID 2378479 reaction equation
[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-])=O.C(O)(=O)C.O>C1COCC1.[Fe]>[CH3:1][C:2]1[C:7]2=[N:8][S:9][N:10]=[C:6]2[CH:5]=[CH:4][C:3]=1[NH2:11]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 6764462,1,3-Benzothiadiazole, 4-methyl-5-nitro-

Product 1

HCID 41871374-Methyl-2,1,3-benzothiadiazol-5-amineYield 92.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

4-Methyl-5-nitro-benzo[1,2,5]thiadiazole (1.4 g, 7.18 mmol) was dissolved in THF (10 mL), acetic acid (1 mL) and water (21 mL) and iron powder (1.4 g, 25.0 mmol, 325 Mesh) was added. The reaction mixture was heated at 80° C. for 1.5 h, cooled to rt and filtered though celite to remove the iron powder. The solution was extracted with CHCl3 (2×250 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to give compound 839C (1.1 g) as a light brown solid.

Workup

  1. temperaturecooled to rt
  2. filtrationfiltered though celite
  3. customto remove the iron powder
  4. extractionThe solution was extracted with CHCl3 (2×250 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a2b054b909f641c8b962990ec3a5cd42
Source dataset
uspto-grants-2008_12
Patent number
US07470797B2

Reaction notes

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