Ethylamine → N-Ethyl 2-{4-[N-methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}propionamide

HRID 1446887Notes

Reaction equation

HRID 1446887 reaction equation
[CH2:1]([NH2:3])[CH3:2].[CH3:4][N:5]([C:16]1[CH:27]=[CH:26][C:19]([O:20][CH:21]([CH3:25])[C:22](Cl)=[O:23])=[CH:18][CH:17]=1)[C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:9]=2[N:10]=1>ClCCl>[CH2:1]([NH:3][C:22](=[O:23])[CH:21]([O:20][C:19]1[CH:18]=[CH:17][C:16]([N:5]([CH3:4])[C:6]2[O:7][C:8]3[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:9]=3[N:10]=2)=[CH:27][CH:26]=1)[CH3:25])[CH3:2]

Participants

4

Reactant 2

HCID 6341Ethylamine2×HCID 205535162-{4-[N-Methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}propionyl chloride

Product 1

HCID 13314826N-Ethyl 2-{4-[N-methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}propionamideYield 68.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A mixture of 70% aqueous ethylamine (0.46 g) and dichloromethane (5 ml) was cooled, with stirring, in an ice bath. A solution of the acid chloride (1.05 g; prepared as described in part (a) above) in dichloromethane (5 ml) was added and the mixture was stirred for 7 hours and then allowed to stand overnight. After this time thin layer chromatography indicated that the reaction had not gone to completion and therefore a further portion of 70% aqueous ethylamine was added and the mixture was heated under reflux for a period of 3 hours. The mixture was allowed to cool, made up to 30 ml with dichloromethane and was washed with water (4×20 ml). The organic phase was dried over anhydrous magnesium sulfate and the solvent removed by evaporation. The solid residue was purified by preparative thin layer chromatography on silica gel (eluent dichloromethane/isopropyl alcohol 20:1) to give the title compound (0.74 g), mp 141°-142° C. The pmr spectrum of the compound was consistent with the assigned structure.

Workup

  1. temperaturewas cooled
  2. stirringthe mixture was stirred for 7 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for a period of 3 hours
  5. temperatureto cool
  6. washwas washed with water (4×20 ml)
  7. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  8. customthe solvent removed by evaporation
  9. customThe solid residue was purified by preparative thin layer chromatography on silica gel (eluent dichloromethane/isopropyl alcohol 20:1)

Sources & evidence

ORD record
ord-dbe42ae3315a43b8b0c9ba4312b3e19c
Source dataset
uspto-grants-1982_02
Patent number
US04314065

Reaction notes

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