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

HRID 2110497Notes

Reaction equation

HRID 2110497 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-ca96d3e8ca28494aae34dab7f57eb4f6
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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