Hydrochloric Acid → HCID 18369530, compound

HRID 1595275Notes

Reaction equation

HRID 1595275 reaction equation
Cl.[CH3:2][N:3]([CH3:18])[C:4]1[S:5][CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[N:8]=1>CCO.[Fe]>[CH3:2][N:3]([CH3:18])[C:4]1[S:5][CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[N:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 824462HCID 824462, compound

Product 1

HCID 18369530HCID 18369530, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Iron powder (6.51 g, 116.7 mmol) and 1N aqueous HCl (2.3 mL) were added to a solution of N,N-dimethyl-4-(4-nitrophenyl)-2-thiazolamine of section a) (2.91 g, 11.7 mmol) in EtOH (39 mL) at room temperature. The mixture was stirred and heated at reflux for 3 h. The hot reaction mixture was filtered through diatomaceous earth. The solid on the filter was washed with hot EtOH (200 mL). The filtrate was diluted with EtOAc and Et2O (1:1, 100 mL) and then concentrated to about 25% of its original volume. This solution was diluted with EtOAc (150 mL). The mixture was washed successively with saturated aqueous NaHCO3, H2O and brine, then dried (MgSO4) and concentrated under reduced pressure to give N,N-dimethyl-4-(4-aminophenyl)-2-thiazolamine (2.24 g, 87% yield) as a light brown oil: 1H NMR (400 MHz, DMSO-d6) δ7.53 (d, J=8.4 Hz, 2H), 6.74 (s, 1H), 6.56 (d, J=8.4 Hz, 2H), 5.16 (s, 2H), 3.05 (s, 6H); MS (FAB) m/z 220 (MH)+. This product was used without further purification in the next section.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. filtrationThe hot reaction mixture was filtered through diatomaceous earth
  4. washThe solid on the filter was washed with hot EtOH (200 mL)
  5. additionThe filtrate was diluted with EtOAc and Et2O (1:1, 100 mL)
  6. concentrationconcentrated to about 25% of its original volume
  7. additionThis solution was diluted with EtOAc (150 mL)
  8. washThe mixture was washed successively with saturated aqueous NaHCO3, H2O and brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8ef342bcab834753b1a9222aae3843e0
Source dataset
uspto-grants-2001_09
Patent number
US06288091B1

Reaction notes

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