Sodium Bicarbonate → HCID 23452994, compound

HRID 1277625Notes

Reaction equation

HRID 1277625 reaction equation
[N:1]([O-])=O.[Na+].[CH2:5]([N:12]1[C:17]([CH3:18])=[N:16][C:15](=[O:19])[C:14]([CH:20](C)C(NN)=O)=[N:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)(O)[O-].[Na+]>O.Cl>[NH2:1][CH2:20][C:14]1[C:15](=[O:19])[NH:16][CH:17]([CH3:18])[N:12]([CH2:5][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:13]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 86737856HCID 86737856, compound

Product 1

HCID 23452994HCID 23452994, compoundYield 108.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

Sodium nitrite (1.29 g) in water (25 ml) was added to a stirred solution of 2-benzyl-2,5-dihydro-3,α-dimethyl-5-oxo-1,2,4-triazine-6-acetic acid, hydrazide (5.0 g) in conc. hydrochloric acid (3.3 ml) and water (75 ml) keeping the temperature at -1° to -2°. The azide separated as a white solid which rapidly became a thick gum. Conc. hydrochloric acid (5 ml) was added and the mixture was raised to 65° over 30 minutes and left at this temperature for 2 hours. During this period the gum gradually dissolved to give a clear yellow solution. This was cooled and brought to pH 8 by the addition of sodium bicarbonate. Water was removed by rotary evaporation and the residual solid was extracted with boiling isopropanol (6×100 ml). The extract was filtered and concentrated to give the amine as a gum (4.37 g) which failed to crystallise.

Workup

  1. customat -1° to -2°
  2. customThe azide separated as a white solid which
  3. additionConc. hydrochloric acid (5 ml) was added
  4. temperaturethe mixture was raised to 65° over 30 minutes
  5. dissolutionDuring this period the gum gradually dissolved
  6. customto give a clear yellow solution
  7. temperatureThis was cooled
  8. customWater was removed by rotary evaporation
  9. extractionthe residual solid was extracted with boiling isopropanol (6×100 ml)
  10. filtrationThe extract was filtered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-71c77ecc12174cac8845183db5950c17
Source dataset
uspto-grants-1981_07
Patent number
US04278673

Reaction notes

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