Dimethylformamide → HCID 178428537, compound

HRID 1995350Notes

Reaction equation

HRID 1995350 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=O)[CH:3]=1.CN(C)C=O.[NH2:16][C:17]1[NH:21][N:20]=[N:19][N:18]=1>O1CCCC1>[NH:18]1[C:17]([NH:16][C:8]([C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=2)=[O:10])=[N:21][N:20]=[N:19]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 27628204-Methylpyridine-2-carboxylic acidHCID 178509299HCID 178509299, compound

Product 1

HCID 178428537HCID 178428537, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.06 g of 4-methyl-2-pyridinecarboxylic acid, 1.28 g of N,N'-carbonyldiimidazole, 25 ml of dimethylformamide and 12 ml of tetrahydrofuran is stirred at room temperature for 3 hours. 0.72 g of 5-aminotetrazole is added to the mixture and said mixture is stirred at 80° C. for 3 hours. Then, the reaction mixture is concentrated under reduced pressure to remove solvent. Water is added to the residue, and the aqueous mixture is adjusted to pH 2 with 10% hydrochloric acid. The crystalline precipitates are collected by filtration, washed with water and then recrystallized from a mixture of dimethylformamide and water. 0.52 g of N-(5-tetrazolyl)-4-methyl-2-pyridinecarboxamide is thereby obtained.

Workup

  1. stirringis stirred at 80° C. for 3 hours
  2. concentrationThen, the reaction mixture is concentrated under reduced pressure
  3. customto remove solvent
  4. additionWater is added to the residue
  5. customThe crystalline precipitates
  6. filtrationare collected by filtration
  7. washwashed with water
  8. customrecrystallized from a mixture of dimethylformamide and water

Sources & evidence

ORD record
ord-ea4de0ec9a424d4cb6f237a0587287c8
Source dataset
uspto-grants-1983_09
Patent number
US04404214

Reaction notes

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