Ammonia → HCID 178437904, compound

HRID 1982346Notes

Reaction equation

HRID 1982346 reaction equation
C([N:8]1[C:12]([CH2:13][CH3:14])=[C:11]([C:15]([OH:17])=[O:16])[N:10]=[N:9]1)C1C=CC=CC=1.N.[Na].C(=O)([O-])[O-].[NH4+].[NH4+]>>[CH2:13]([C:12]1[NH:8][N:9]=[N:10][C:11]=1[C:15]([OH:17])=[O:16])[CH3:14]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 517111Ammonium CarbonateHCID 5360545SodiumHCID 13646828HCID 13646828, compound

Product 1

HCID 178437904HCID 178437904, compound

Procedure

To a mixture of 24 g (104 mmoles) of 1(2 or 3)-benzyl-5-ethyl-1H-1,2,3-triazole-4-carboxylic acid in 250 ml of liquid ammonia at -78° C., 7.2 g (312 mmoles) of sodium pellets were added, in portions, until the solution maintained a dark blue color. The reaction was then quenched, with 10 g (128 mmoles) of ammonium carbonate. The resulting yellow mixture was allowed to warm to room temperature and the ammonia evaporated. The solid residue was dissolved in 70 ml of water and extracted with ether. The aqueous phase was then adjusted to pH 1 with 12N hydrochloric acid and 140.0 g (95%) of 5-ethyl-1H-1,2,3-triazole-4-carboxylic acid was precipitated as a yellow solid. The structure was confirmed by n.m.r. and I.R.

Workup

  1. temperaturemaintained a dark blue color
  2. customthe ammonia evaporated
  3. dissolutionThe solid residue was dissolved in 70 ml of water
  4. extractionextracted with ether
  5. customwas precipitated as a yellow solid

Sources & evidence

ORD record
ord-6a357ed05c964bf6b9d2269a962ae4d8
Source dataset
uspto-grants-1986_06
Patent number
US04596596

Reaction notes

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