Sodium Hydroxide → HCID 178513172, compound

HRID 1289758Notes

Reaction equation

HRID 1289758 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][N:3]=1.S(Cl)(Cl)=O.[C:15]([NH:18][NH2:19])([NH2:17])=[NH:16].Cl.[OH-].[Na+]>ClCCl.CN(C)C=O>[C:15]([NH:18][NH:19][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[N:3][CH:4]=1)(=[NH:16])[NH2:17]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 792226-Chloronicotinic acidHCID 178418668HCID 178418668, compound

Product 1

HCID 178513172HCID 178513172, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-chloronicotinic acid (10.0 g) in dichloromethane (100 ml) was added dropwise dimethylformamide (10 ml) and thionyl chloride (5.1 ml), and the mixture was stirred for 1 hour with refluxing. The resulting reaction mixture was dropwise added to aminoguanidine hydrochloride (24.6 g) in a 2.2N aqueous sodium hydroxide solution (100 ml) under ice-cooling. After the dropwise addition, the mixture was stirred at said temperature for 10 minutes to give 6.87 g of a pale-brown solid by filtration (yield 51%).

Workup

  1. temperaturewith refluxing
  2. customThe resulting reaction mixture
  3. temperaturecooling
  4. additionAfter the dropwise addition
  5. stirringthe mixture was stirred
  6. customfor 10 minutes

Sources & evidence

ORD record
ord-4e871989bc824920a3a5d9fb51a60184
Source dataset
uspto-grants-1998_05
Patent number
US05750545

Reaction notes

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