Water → 2,1,3-Benzothiadiazol-5-amine

HRID 2095155Notes

Reaction equation

HRID 2095155 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-c9ad7ee22ec041f3bd1f495fd2a48b74
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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