Acetic Acid → Benzothiazol-5-amine

HRID 888103Notes

Reaction equation

HRID 888103 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][CH:10]=[N:9][C:8]=2[CH:12]=1)([O-])=O.CC(O)=O>C1COCC1.[Zn]>[S:11]1[C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:12][C:8]=2[N:9]=[CH:10]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 3501355-Nitrobenzothiazole

Product 1

HCID 70749Benzothiazol-5-amine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5-Nitrobenzo[d]thiazole (150 mg) was dissolved in THF (20 mL) at 0° C. and AcOH (1 mL) was added followed by Zinc dust (1.65 g). Mixture was stirred at RT for 1 h and was filtered on silica pad (rinsed with EtOAc). Solvent was evaporated, residue was diluted with NaHCO3 and extracted with EtOAc. Organic phases was dried, filtered and evaporated to give benzo[d]thiazol-5-amine.

Workup

  1. filtrationwas filtered on silica pad (rinsed with EtOAc)
  2. customSolvent was evaporated
  3. additionresidue was diluted with NaHCO3
  4. extractionextracted with EtOAc
  5. customOrganic phases was dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-37ce42887c0b44eba46289f031e104e5
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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