Dibutylamine → HCID 19811636, compound

HRID 373116Notes

Reaction equation

HRID 373116 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.[CH2:13]([NH:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16]>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([N:17]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:13][CH2:14][CH2:15][CH3:16])=[O:4]

Participants

6

Reactant 2

HCID 8148DibutylamineHCID 8359Isatoic Anhydride

Product 1

HCID 19811636HCID 19811636, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

2.0 g isatoic anhydride is dissolved in 50 ml methylene chloride/5 ml dimethylformamide and 1.87 g 4-dimethylaminopyridine and 1.98 g dibutylamine are added. The mixture is stirred at room temperature for 5 hours, then diluted with 250 ml of ethyl acetate. The organic solution is washed with 10% HCl and brine and dried over sodium sulfate followed by filtration and evaporation to obtain a residue. The residue is dissolved in 25 ml ethyl acetate, the solution filtered, concentrated and this residue purified by flash chromatography on silica gel in ethyl acetate/hexane, 2:3, to give 2-amino-N,N-dibutyl benzamide.

Workup

  1. washThe organic solution is washed with 10% HCl and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfollowed by filtration and evaporation
  4. customto obtain a residue
  5. filtrationthe solution filtered
  6. concentrationconcentrated
  7. customthis residue purified by flash chromatography on silica gel in ethyl acetate/hexane, 2:3

Sources & evidence

ORD record
ord-114a506e0db34436ab0d24ef78fab666
Source dataset
uspto-grants-1992_11
Patent number
US05162336

Reaction notes

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