Water → 2,1,3-Benzothiadiazol-5-amine

HRID 2212859Notes

Reaction equation

HRID 2212859 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-b77dcfaf9bf74f65934b5a592ad8d116
Source dataset
uspto-grants-2006_09
Patent number
US07105503B2

Reaction notes

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