Water → 2,1,3-Benzothiadiazol-5-amine

HRID 254989Notes

Reaction equation

HRID 254989 reaction equation
O.[N+:2]([C:5]1[CH:13]=[CH:12][C:8]2=[N:9][S:10][N:11]=[C:7]2[CH:6]=1)([O-])=O>C1COCC1.[Zn]>[N:9]1[S:10][N:11]=[C:7]2[CH:6]=[C:5]([NH2:2])[CH:13]=[CH:12][C:8]=12

Participants

5

Reactant 2

HCID 962WaterHCID 2978975-Nitro-2,1,3-benzothiadiazole

Product 1

HCID 3143132,1,3-Benzothiadiazol-5-amineYield 47.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of MoCl5 (8 g) in 50 ml of THF was added 10 ml of H2O and followed by the addition of Zn dust (3 g) 5 minutes later. 5-Nitrobenzo-2,1,3-thiadiazole (1.0 g) was then added to this mixture and the resulting reaction mixture was kept under reflux for 20 minutes. Benzo[1,2,5]thiadiazol-5-ylamine (0.4 g) was isolated by filtration and purified by column chromatography to be used in the next step.

Workup

  1. customthe resulting reaction mixture
  2. temperatureunder reflux for 20 minutes

Sources & evidence

ORD record
ord-90d1ab0d08e848c7ad5d08aef55c54b7
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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