3,4-Diaminopyridine → HCID 178493307, compound

HRID 2309875Notes

Reaction equation

HRID 2309875 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH2:8].[CH3:9][O:10][C:11]1[CH:19]=[C:18]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:17]=[CH:16][C:12]=1[C:13](O)=O>P(Cl)(Cl)(Cl)=O>[CH3:9][O:10][C:11]1[CH:19]=[C:18]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:17]=[CH:16][C:12]=1[C:13]1[NH:8][C:7]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 59183,4-DiaminopyridineHCID 121193062-Methoxy-4-[(methylsulfonyl)amino]benzoic acid

Product 1

HCID 178493307HCID 178493307, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

Quantities of 5.45 gm (50 mmol) of 3,4-diaminopyridine and 12.25 gm (50 mmol) of 2-methoxy-4-methanesulfonylaminobenzoic acid were triturated together and refluxed for four hours in 300 ml of phosphorus oxychloride. Excess phosphorus oxychloride was then distilled off, and the residue was mixed with 500 ml of water and adjusted to a pH of 8 with concentrated ammonia. The insoluble components were filtered off, the filtrate was saturated with sodium chloride, and the crude product precipitated. After purification by chromatography (800 gm of aluminum oxide: eluant: dichloromethane with 5 to 10% of ethanol), 4.8 gm (25.2% of theory) were obtained.

Workup

  1. distillationExcess phosphorus oxychloride was then distilled off
  2. additionthe residue was mixed with 500 ml of water
  3. filtrationThe insoluble components were filtered off
  4. customthe crude product precipitated
  5. customAfter purification by chromatography (800 gm of aluminum oxide: eluant: dichloromethane with 5 to 10% of ethanol)
  6. custom4.8 gm (25.2% of theory) were obtained

Sources & evidence

ORD record
ord-d21494a0e0e741168db5f3419ec53e68
Source dataset
uspto-grants-1987_09
Patent number
US04696931

Reaction notes

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