Triethylamine → 4D-083

HRID 1995344Notes

Reaction equation

HRID 1995344 reaction equation
[O:1]=[C:2]1[C:7]([C:8](O)=[O:9])=[CH:6][C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:4][NH:3]1.C([N:19](CC)CC)C.S(Cl)(Cl)=O>O1CCCC1>[O:1]=[C:2]1[C:7]([C:8]([NH2:19])=[O:9])=[CH:6][C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:4][NH:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 121489343-Oxo-6-phenyl-2,3-dihydropyridazine-4-carboxylic acid

Product 1

HCID 14753284D-083

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an alternate procedure, a mixture of 2,3-dihydro-3-oxo-6-phenyl-4-pyridazinecarboxylic acid (1.92 g), triethylamine (3.0 ml), and thionyl chloride (5.0 ml) in tetrahydrofuran is allowed to stir at 20°-25° C. for 6 hours. The mixture is concentrated on the rotary evaporator and the residue is treated with 50 ml of cold ammonium hydroxide solution. The solid product is collected and recrystallized from acetic acid to give 2,3-dihydro-3-oxo-6-phenyl-4-pyridazinecarboxamide.

Workup

  1. concentrationThe mixture is concentrated on the rotary evaporator
  2. additionthe residue is treated with 50 ml of cold ammonium hydroxide solution
  3. customThe solid product is collected
  4. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-091ee31fa94a4af29767edc1a3780f19
Source dataset
uspto-grants-1983_09
Patent number
US04404203

Reaction notes

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