Acetic Acid → 2-Methylbenzo[d]thiazol-7-amine

HRID 620120Notes

Reaction equation

HRID 620120 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.C(O)(=O)C>C(O)C.[Fe]>[CH3:1][C:2]1[S:3][C:4]2[C:10]([NH2:11])=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 2764082-Methyl-7-nitro-1,3-benzothiazole

Product 1

HCID 138244302-Methylbenzo[d]thiazol-7-amineYield 68.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3.8 g of the product from Example 6 and 8.1 g of glacial acetic acid in 56 mL absolute ethanol at reflux temperature was added 3.8 g of iron powder in small portions. The reaction mixture was heated at reflux temperature for about 36 hours, and was then cooled and filtered. The filtrate was concentrated in vacuo and the residue treated with several mL cold water to give a solid. Filtration and drying gave 2.2 g of the title compound as a tan-colored solid, m.p. 100°-101° C.; NMR (CDCl3): δ 2.8 (3H, s), 3.9 (2H, br s), 6.65 (1H, d, J=8 Hz), 7.2 (1H, t, J=8 Hz), 7.5 (1H, d, J=8 Hz).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for about 36 hours
  3. temperaturewas then cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. additionthe residue treated with several mL cold water
  7. customto give a solid
  8. filtrationFiltration
  9. customdrying

Sources & evidence

ORD record
ord-3a33860c24b84efb96d85e611b174927
Source dataset
uspto-grants-1989_04
Patent number
US04820332

Reaction notes

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