Water → 2,1,3-Benzothiadiazol-5-amine

HRID 2229918Notes

Reaction equation

HRID 2229918 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2=[N:8][S:9][N:10]=[C:6]2[CH:5]=1)([O-])=O.Cl[Sn]Cl.O>O1CCOCC1.C(O)C>[NH2:1][C:4]1[CH:12]=[CH:11][C:7]2=[N:8][S:9][N:10]=[C:6]2[CH:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24479Stannous ChlorideHCID 2978975-Nitro-2,1,3-benzothiadiazole

Product 1

HCID 3143132,1,3-Benzothiadiazol-5-amineYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-nitrobenzo-2,1,3-thiadiazole in a mixture of dioxane (22 mL) and ethanol (22 mL) at RT added solid SnCl2 followed by addition of water (1 mL). The reaction mixture was warmed up to 50° C. and stirred for 10 min, cooled to RT, concentrated and partitioned between ethyl acetate/1N NaOH. The organic layer was washed with 1N NaOH, water, brine, dried over MgSO4 and charcoal. Evaporation of the solvent gave 5-aminobenzo-2,1,3-thiadiazole as a yellow powder (3.0 g, 88%).

Workup

  1. temperaturecooled to RT
  2. concentrationconcentrated
  3. custompartitioned between ethyl acetate/1N NaOH
  4. washThe organic layer was washed with 1N NaOH, water, brine
  5. dry with materialdried over MgSO4 and charcoal
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-62aca560783c4d35bac56c04f82023ed
Source dataset
uspto-grants-2002_07
Patent number
US06420567B1

Reaction notes

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