Ammonium Chloride → HCID 178524458, compound

HRID 2083201Notes

Reaction equation

HRID 2083201 reaction equation
[C:1]([C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[N:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)#[N:2].[Cl-].[NH4+].[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C)C=O>[NH:21]1[C:1]([C:3]2[CH:4]=[CH:5][C:6]([O:7][C:8]3[N:16]=[CH:15][CH:14]=[CH:13][C:9]=3[C:10]([OH:12])=[O:11])=[CH:17][CH:18]=2)=[N:2][N:23]=[N:22]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 13209512HCID 13209512, compound

Product 1

HCID 178524458HCID 178524458, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 14.5 g of 2-(4-cyanophenoxy)nicotinic acid, 3.97 g of ammonium chloride, 4.96 g of sodium azide and 120 ml of dimethylformamide is allowed to stand at 100° C to 110° C for 24 hours. After cooling, the reaction mixture is filtered, and the filtrate is concentrated. To the residue is added a dilute hydrochloric acid, and the crystals are filtered off and recrystallized from methanol to give 5 g of 2-[4-(5-1H-tetrazolyl)phenoxy]-nicotinic acid melting at 225° C to 230° C with decomposition.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated
  4. additionTo the residue is added a dilute hydrochloric acid
  5. filtrationthe crystals are filtered off
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-e0cfe1dc57724741bb88b92ae3819f37
Source dataset
uspto-grants-1978_04
Patent number
US04085111

Reaction notes

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