2,4,6-Trimethoxyaniline → 2-(4-n-Propylphenylthio)-N-(2,4,6-trimethoxyphenyl)nonanamide

HRID 2257159Notes

Reaction equation

HRID 2257159 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:12]([OH:14])=O)=[CH:6][CH:5]=1)[CH2:2][CH3:3].[CH3:22][O:23][C:24]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[C:27]([O:33][CH3:34])[C:25]=1[NH2:26]>S(Cl)(Cl)=O.C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10][CH:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:12]([NH:26][C:25]2[C:27]([O:33][CH3:34])=[CH:28][C:29]([O:31][CH3:32])=[CH:30][C:24]=2[O:23][CH3:22])=[O:14])=[CH:8][CH:9]=1)[CH2:2][CH3:3]

Participants

6

Reactant 2

HCID 842712,4,6-TrimethoxyanilineHCID 149953862-(4-n-Propylphenylthio)nonanoic acid

Product 1

HCID 149953872-(4-n-Propylphenylthio)-N-(2,4,6-trimethoxyphenyl)nonanamideYield 49%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

1.54 g (5 mmole) of the title compound of Example 3 in 20 ml of thionyl chloride was refluxed for 3 hours and then concentrated to dryness in vacuo. 523 mg (1.6 mmole) of the resulting acid chloride was dissolved in 20 ml methylene chloride and to the solution was added 292 mg (1.6. mmole) 2,4,6-trimethoxyaniline and 195 mg (1.6 mmole) 4-dimethylaminopyridine. The resulting solution was stirred at room temperature overnight and then concentrated in vacuo. The residue was partitioned between 60 ml ethyl acetate and 20 ml 1N aqueous hydrochloric acid solution. The ethyl acetate layer was washed with 50 ml water and 50 ml saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The crude product was chromatographed on 100 g silica gel, eluting with 1:1 hexane/ethyl acetate to yield 370 mg (49% yield) of the title compound as a whitish solid.

Workup

  1. concentrationconcentrated to dryness in vacuo
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between 60 ml ethyl acetate and 20 ml 1N aqueous hydrochloric acid solution
  4. washThe ethyl acetate layer was washed with 50 ml water and 50 ml saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product was chromatographed on 100 g silica gel
  8. washeluting with 1:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-e0ddbdc6002d450d81f01f3cd0be65f6
Source dataset
uspto-grants-1997_08
Patent number
US05656634

Reaction notes

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