Ethanol → 5,7-Dimethyl-2,1,3-benzothiadiazol-4-amine

HRID 353698Notes

Reaction equation

HRID 353698 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:5]2=[N:6][S:7][N:8]=[C:4]2[C:3]=1[N+:12]([O-])=O.C(O)C.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[NH2:12][C:3]1[C:4]2[C:5](=[N:6][S:7][N:8]=2)[C:9]([CH3:11])=[CH:10][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 702EthanolHCID 24489Sodium DithioniteHCID 235115395,7-Dimethyl-4-nitro-2,1,3-benzothiadiazole

Product 1

HCID 120599585,7-Dimethyl-2,1,3-benzothiadiazol-4-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5,7-Dimethyl-4-nitro-2,1,3-benzothiadiazole (20 g) is warmed to ebullition in water (2.2 l) and ethanol (2.2 l) and sodium dithionite is added portionwise (strongly exothermic reaction). The reaction mixture is immediately cooled in an ice bath and extracted with ethyl acetate. The organic phase is concentrated by evaporation and the residue recrystallised in water to give 4-amino-5,7-dimethyl-2,1,3-benzothiadiazole. Mp=113-114°.

Workup

  1. customstrongly exothermic reaction)
  2. temperatureThe reaction mixture is immediately cooled in an ice bath
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic phase is concentrated by evaporation
  5. customthe residue recrystallised in water

Sources & evidence

ORD record
ord-e5e7b9d1e022410698d2ae555157909d
Source dataset
uspto-grants-2004_06
Patent number
US06756367B2

Reaction notes

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