Dimethyl Sulfoxide → HCID 57272073, compound

HRID 1263319Notes

Reaction equation

HRID 1263319 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]2[CH:9]([CH3:15])[CH2:10][CH2:11][C:12](Br)(Br)[C:5]2=[N:4][CH:3]=1.CS(C)=O.[C:20]1([NH:26][NH2:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O>[Br:1][C:2]1[C:7](=[O:8])[N:6]2[CH:9]([CH3:15])[CH2:10][CH2:11][C:12](=[N:27][NH:26][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 7516PhenylhydrazineHCID 13312960HCID 13312960, compound

Product 1

HCID 57272073HCID 57272073, compoundYield 34.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.0 g. (0.01 moles) of 3,9,9-tribromo-6-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-4-one are dissolved in 10 ml. of dimethyl sulfoxide. To the solution 2.8 ml. (0.03 moles) of phenylhydrazine are added. The reaction mixture is allowed to stand for three days whereupon 20 ml. of water are added. The solvent is decanted from the precipitated substance and the product is recrystallized from methanol. 1.3 g. (34.7%) of 3-bromo-9-(phenylhydrazono)-6-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-4-one are obtained, melting at 190° to 192° C.

Workup

  1. customThe solvent is decanted from the precipitated substance
  2. customthe product is recrystallized from methanol

Sources & evidence

ORD record
ord-0d42d939fcd44da9a5c9318a38c1c8f9
Source dataset
uspto-grants-1984_06
Patent number
US04456752

Reaction notes

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