2,3-Diaminopyridine → HCID 178493630, compound

HRID 1380719Notes

Reaction equation

HRID 1380719 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([S:12]([Cl:15])(=[O:14])=[O:13])[CH:9]=[CH:8][C:4]=1[C:5](O)=O.[NH2:16]C1C=CC(C(O)=O)=C(OC)C=1.N[C:29]1[C:34]([NH2:35])=[CH:33][CH:32]=[CH:31][N:30]=1>P(Cl)(Cl)(Cl)=O>[ClH:15].[CH3:1][O:2][C:3]1[CH:11]=[C:10]([S:12]([Cl:15])(=[O:14])=[O:13])[CH:9]=[CH:8][C:4]=1[C:5]1[NH:16][C:33]2=[CH:32][CH:31]=[N:30][CH:29]=[C:34]2[N:35]=1

Participants

5

Reactant 3

HCID 99562,3-DiaminopyridineHCID 755994-Amino-o-anisic acidHCID 201845804-(Chlorosulfonyl)-2-methoxybenzoic acid

Product 1

HCID 178493630HCID 178493630, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
80 °C

Procedure

Five grams of 2-methoxy-4-chlorosulfonyl-benzoic acid (prepared from 4-amino-2-methoxy-benzoic acid via the corresponding diazonium compound) were dissolved in 400 ml of phosphorus oxychloride and heated to 80° C. for 30 minutes. Then, 3.6 gm of 2,3-diaminopyridine were added, and the mixture was refluxed for four hours. The reaction mixture was concentrated by evaporation in vacuo and re-evaporated with toluene, and the solid residue was processed further without any other purification.

Workup

  1. temperaturethe mixture was refluxed for four hours
  2. concentrationThe reaction mixture was concentrated by evaporation in vacuo
  3. customre-evaporated with toluene
  4. customthe solid residue was processed further without any other purification

Sources & evidence

ORD record
ord-94633bad767d4d8fbfd17521349fbbb8
Source dataset
uspto-grants-1986_04
Patent number
US04582837

Reaction notes

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