Hydrochloric Acid → HCID 14051003, compound

HRID 1762157Notes

Reaction equation

HRID 1762157 reaction equation
[CH3:1][C:2]1[C:7](C(O)=O)=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[CH:5]=[C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:3]=1.C1(P([N:40]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:43][N:44]([CH3:48])[CH2:45][CH2:46][NH2:47].Cl.C([O:53][CH2:54]C)(=O)C>C1C=CC=CC=1.O.C(N(CC)CC)C>[CH3:43][N:44]([CH3:48])[CH2:45][CH2:46][NH:47][C:54](=[O:53])[NH:40][C:7]1[C:2]([CH3:1])=[N:3][C:4]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:5][C:6]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 66053N,N-DimethylethylenediamineHCID 199401P,P-Diphenylphosphinic azideHCID 104720472-Methyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylic acid

Product 1

HCID 14051003HCID 14051003, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 2-methyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylic acid (5 g), triethylamine (1.5 g) and diphenylphosphorylazide (4.1 g) in benzene (50 ml) was refluxed for 2 hours. To the reaction mixture was added 2-dimethylaminoethylamine (1.6 g) and the mixture was further refluxed for 2 hours. After allowing to cool at ambient temperature, the reaction mixture was poured into a mixture of ethyl acetate (100 ml) and water (100 ml). The reaction mixture was adjusted to pH 2.0 with 10% hydrochloric acid. The aqueous layer was separated, washed with methylene chloride (100 ml) and adjusted to pH 9.0 with 10% aqueous sodium hydroxide. The resulting precipitates were collected by filtration, washed with water and dried in vacuo to give 3-[3-(2-dimethylaminoethyl)ureido]-2-methyl-4-(3-nitrophenyl)-6-phenylpyridine (1.87 g).

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperaturethe mixture was further refluxed for 2 hours
  3. customThe aqueous layer was separated
  4. washwashed with methylene chloride (100 ml)
  5. customThe resulting precipitates
  6. filtrationwere collected by filtration
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-1b2b691176e64126992ba0b1d2fba8c0
Source dataset
uspto-grants-1989_05
Patent number
US04831030

Reaction notes

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