Hydrochloric Acid → HCID 136133180, compound

HRID 1914827Notes

Reaction equation

HRID 1914827 reaction equation
[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[CH:4][C:3]=1C(NN)=O.C[CH2:17][OH:18].Cl.[N:20]([O-])=O.[Na+]>O>[CH3:11][C:9]1[CH:10]=[C:6]2[N:5]=[CH:4][C:3]3[NH:20][C:17](=[O:18])[NH:1][C:2]=3[N:7]2[N:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 23668193Sodium NitriteHCID 58034303HCID 58034303, compound

Product 1

HCID 136133180HCID 136133180, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A 100 mL flask containing Compound (10-1) (1.1 g, 5.0 mmol, 1 eq.), EtOH (25 mL), and 10% aqueous HCl (25 mL) was cooled to 0° C. by ice-water bath. Then NaNO2 (0.35 g, 5.0 mmol, 1 eq.) in water (8 mL) was added slowly. The mixture was stirred at that temperature for 2 hours, after which it was heated to 80° C. for 2 hours. After cooling and removal of the volatiles by rotary evaporation, the residue was treated with water (40 mL). The resulting precipitated solid was filtered and washed with water (2×5 mL) to provide Compound (10-2) as a brownish solid.

Workup

  1. temperatureafter which it was heated to 80° C. for 2 hours
  2. temperatureAfter cooling
  3. customremoval of the volatiles
  4. customby rotary evaporation
  5. additionthe residue was treated with water (40 mL)
  6. customThe resulting precipitated solid
  7. filtrationwas filtered
  8. washwashed with water (2×5 mL)

Sources & evidence

ORD record
ord-c19b6c33ae58436e908a70db48248174
Source dataset
uspto-grants-2013_12
Patent number
US08614221B2

Reaction notes

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