Dimethylamine → HCID 178470200, compound

HRID 1076158Notes

Reaction equation

HRID 1076158 reaction equation
Cl.[C:2]([C:7]1[N:8]=[C:9]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[NH:10][C:11]=1[NH2:12])([O:4][CH2:5][CH3:6])=[O:3].[N:19]([O-])=O.[Na+].[CH3:23][NH:24][CH3:25].C(=O)([O-])[O-].[Na+].[Na+]>Cl.O>[C:2]([C:7]1[N:8]=[C:9]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[NH:10][C:11]=1[N:12]=[N:19][N:24]([CH3:25])[CH3:23])([O:4][CH2:5][CH3:6])=[O:3]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 10340Sodium CarbonateHCID 23668193Sodium NitriteHCID 178470199HCID 178470199, compound

Product 1

HCID 178470200HCID 178470200, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

4-Carbethoxy-5-amino-2-(3-pyridyl)imidazole hydrochloride (1.90 gm) was dissolved in 5N hydrochloric acid (10 mls) and the mixture stirred at room temperature. A solution of sodium nitrite (0.5 gm) in water (5 ml) was then added in small portions, and the resulting clear solution stirred for 5 minutes. The mixture was then poured into a vigorously stirred mixture of 30% aqueous dimethylamine (1.0 ml) and 10% aqueous sodium carbonate (20 mls) giving a pale brown precipitate. The crude product was recrystallized from methanol/ether to give 0.65 gm of an off-white solid mp. 125° with decomposition.

Workup

  1. stirringthe resulting clear solution stirred for 5 minutes
  2. customgiving a pale brown precipitate
  3. customThe crude product was recrystallized from methanol/ether

Sources & evidence

ORD record
ord-18864bc27244428aa164bebf583c792e
Source dataset
uspto-grants-1976_05
Patent number
US03956262

Reaction notes

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