Hydrochloric Acid → HCID 54153306, compound

HRID 1973340Notes

Reaction equation

HRID 1973340 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:5]([CH3:12])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].Cl.[N:21]([O-])=O.[Na+].C([O-])([O-])=O.[Na+].[Na+].[CH3:31][NH:32][CH3:33]>O>[CH2:13]([C:4]1[N:5]([CH3:12])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]([N:1]=[N:21][N:32]([CH3:33])[CH3:31])[N:3]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 10340Sodium CarbonateHCID 11357395HCID 11357395, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 54153306HCID 54153306, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

4-Amino-2-benzyl-5-carbethoxy-1-methyl-imidazole (30g.) was suspended in water (12 ml.) containing conc. HCl -- (12 ml) and a solution of sodium nitrite (0.96 g.) in water (5 ml.) slowly added with stirring at 0° C. After addition was complete this solution was added to a stirred solution of Na2CO3 (118 ml, 30%) and aqueous dimethylamine (2.5 ml, 25%) added dropwise at 0° C added with stirring. After half an hour the brown precipitate was filtered off, washed with water and dried. Crystallisation from ethylacetate/petrol yielded 2-benzyl-5-carbethoxy-(3,3-dimethyltriazeno)-1-methylimidazole (1g, 27%) m.p. 107°-108° C (dec).

Workup

  1. additionAfter addition
  2. additionadded dropwise at 0° C
  3. additionadded
  4. stirringwith stirring
  5. filtrationAfter half an hour the brown precipitate was filtered off
  6. washwashed with water
  7. customdried
  8. customCrystallisation from ethylacetate/petrol

Sources & evidence

ORD record
ord-b38058a48e8c44d797e3408e3826c06d
Source dataset
uspto-grants-1976_12
Patent number
US03997518

Reaction notes

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