Hydrochloric Acid → 4-Methyl-5-(p-nitrophenyl)-2-thiazolamine

HRID 908153Notes

Reaction equation

HRID 908153 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:16]C(=O)C)[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1.Cl>C(O)C>[CH3:1][C:2]1[N:3]=[C:4]([NH2:16])[S:5][C:6]=1[C:7]1[CH:8]=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11414740N-[4-Methyl-5-(4-nitro-phenyl)-thiazol-2-yl]-acetamide

Product 1

HCID 6166034-Methyl-5-(p-nitrophenyl)-2-thiazolamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-[4-methyl-5-(4-nitro-phenyl)-thiazol-2-yl]-acetamide (prepared by the method described in J. Liebscher, E. Mitzner, Synthesis, 1985, (4), p 414) (10 g, 36 mmol) in ethanol (200 ml) and 7M hydrochloric acid (50 ml) is heated at reflux with stirring for 4 hours. After standing at room temperature for 4 days the hydrochloride salt of the title compound (8.15 g) precipitates as yellow crystals which are removed by filtration and dried. The title compound (free base) is obtained by partitioning the hydrochloride salt between aqueous sodium hydroxide and ethyl acetate. The organic extract is separated, dried (MgSO4) and the solvent is removed to give an orange solid (6.58 g). 1N nmr (CDCl3): 2.38 (4H, s, Me), 5.02 (2H, br s, NH2), 7.45 (2H, d), 8.20 (2H, d)

Workup

  1. temperatureat reflux
  2. waitAfter standing at room temperature for 4 days
  3. customthe hydrochloride salt of the title compound (8.15 g) precipitates as yellow crystals which
  4. customare removed by filtration
  5. customdried

Sources & evidence

ORD record
ord-820c7a5071784187bb1797aa8b0784b9
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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