Hydrochloric Acid → HCID 68290801, compound

HRID 2205951Notes

Reaction equation

HRID 2205951 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[N:15]([CH3:16])[CH:14]=[N:13][C:12]=2[CH3:17])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].O.Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[N:15]([CH3:16])[CH:14]=[N:13][C:12]=2[CH3:17])[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24489Sodium DithioniteHCID 68291250HCID 68291250, compound

Product 1

HCID 68290801HCID 68290801, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

5-(3-Chloro-4-nitrophenyl)-1,4-dimethyl-1H-imidazole (Preparation 160, 99 mg 0.39 mmole) was stirred in ethanol (3.6 mL) and 1M sodium dithionite in water (1.2 mL, 1.2 mmole) was added. The reaction was heated at 40° C. for 1 hour. 2M Hydrochloric acid (5 mL) was added and the reaction was heated at 50° C. for 1 hour. The solution was cooled and quenched with anhydrous sodium carbonate and the ethanol was evaporated. The solution was saturated with sodium chloride and extracted with ethyl acetate (4×6 mL). The organic layers were dried and evaporated to afford the title compound (62 mg, 71%). 1H-NMR (CD3OD, 500 MHz): δ 2.12 (s, 3H), 3.52 (s, 3H), 6.92 (d, J=8.20, 1H), 7.01 (d, J=1.89, 8.20 Hz, 1H), 7.18 (d, J=1.89 Hz, 1H), 7.53 (s, 1H).

Workup

  1. temperaturethe reaction was heated at 50° C. for 1 hour
  2. temperatureThe solution was cooled
  3. customquenched with anhydrous sodium carbonate
  4. customthe ethanol was evaporated
  5. extractionextracted with ethyl acetate (4×6 mL)
  6. customThe organic layers were dried
  7. customevaporated

Sources & evidence

ORD record
ord-18a7122e2bb64856b407d1f5acc46094
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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