Phosphorus oxychloride → HCID 19921455, compound

HRID 1647897Notes

Reaction equation

HRID 1647897 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][NH:7][C:8](=[O:18])[C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH3:16])=[C:11]([NH2:17])[CH:10]=1)=[O:4].P(Cl)(Cl)(Cl)=O.[C:24]([C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=O)=[CH:28][CH:27]=1)#[N:25]>C(OCC)(=O)C>[C:24]([C:26]1[CH:34]=[CH:33][C:29]([C:30]2[N:15]([CH3:16])[C:12]3[CH:13]=[CH:14][C:9]([C:8]([NH:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[O:18])=[CH:10][C:11]=3[N:17]=2)=[CH:28][CH:27]=1)#[N:25]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 801724-Cyanobenzoyl chlorideHCID 15225626HCID 15225626, compound

Product 1

HCID 19921455HCID 19921455, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

4.7 g of 3-amino-4-methylamino-benzoic acid-[N-(2-methoxycarbonyl-ethyl)-amide] are first stirred at ambient temperature with 40 ml of phosphorusoxychloride, then 3.1 g of 4-cyano-benzoylchloride are added and the mixture is heated to 90° C. for 8 hours. The phosphorusoxychloride is distilled off in vacuo, the residue is stirred into 500 ml of water at 30° C. and neutralised by the addition of sodium bicarbonate in batches. The precipitate is suction filtered and extracted with ethyl acetate. The ethyl acetate phases are evaporated down, the residue is combined with the precipitate and purified by chromatography on silica gel (eluant:ethyl acetate/ethanol=100:1 to 100:5). The product obtained is decocted with ethyl acetate for final purification. Yield: 1,86 g (27% of theory), Rf value: 0.51 (silica gel; ethyl acetate/ethanol=9:1)

Workup

  1. distillationThe phosphorusoxychloride is distilled off in vacuo
  2. additionneutralised by the addition of sodium bicarbonate in batches
  3. filtrationfiltered
  4. extractionextracted with ethyl acetate
  5. customThe ethyl acetate phases are evaporated down
  6. custompurified by chromatography on silica gel (eluant:ethyl acetate/ethanol=100:1 to 100:5)
  7. customThe product obtained
  8. custompurification

Sources & evidence

ORD record
ord-8b67c3c662884c7497ee85ea4ab992cf
Source dataset
uspto-grants-1995_07
Patent number
US05434150

Reaction notes

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