Chloroform → HCID 57050471, compound

HRID 224794Notes

Reaction equation

HRID 224794 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]2[CH:13]([CH3:19])[CH2:14][CH2:15][C:16](=[N:17][NH2:18])[C:9]2=[N:8][CH:7]=1)=[O:5])[CH3:2].C(Cl)(Cl)Cl.C(N(CC)CC)C.[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O>[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]2[CH:13]([CH3:19])[CH2:14][CH2:15][C:16](=[N:17][NH:18][C:31](=[O:38])[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:9]2=[N:8][CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 57060146HCID 57060146, compound

Product 1

HCID 57050471HCID 57050471, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2.0 g. (7.57 millimoles) of ethyl-9-hydrazono-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido(1,2-a)pyrimidine-3-carboxylate and 20 ml. of anhydrous chlorform 1.6 ml. (11.35 millimoles) of triethylamine and 1.3 ml. (11.35 millimoles) of benzoyl chloride are added. The mixture is heated to boiling for 2 hours, whereupon it is cooled to room temperature and thoroughly admixed with 20 ml. of water. The organic phase is separated and the aqueous layer is extracted with 10 ml. of chloroform. The united organic phase is dried over anhydrous sodium sulfate and evaporated in vacuo. The residue is recrystallized from methanol. Thus 1.5 g. (53.8%) of ethyl-9-(benzoyl-hydrazono)-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido(1,2-a)pyrimidine-3-carboxylate are obtained. Mp.: 209°-210° C.

Workup

  1. temperatureThe mixture is heated
  2. customThe organic phase is separated
  3. extractionthe aqueous layer is extracted with 10 ml
  4. dry with materialThe united organic phase is dried over anhydrous sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-dd1e2cfa648e4e4ab0335ece47f201d9
Source dataset
uspto-grants-1980_11
Patent number
US04234586

Reaction notes

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