Dibutylamine → HCID 54231666, compound

HRID 1198895Notes

Reaction equation

HRID 1198895 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]([C:16]3[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=3[C:18]([OH:20])=O)=[O:15])[CH:5]=[CH:4][C:3]1=2.P(Cl)(Cl)Cl.[CH2:30]([NH:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:31][CH2:32][CH3:33]>ClCCl>[CH2:30]([N:34]([CH2:35][CH2:36][CH2:37][CH3:38])[C:18](=[O:20])[C:17]1[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=1[C:14]([C:6]1[CH:5]=[CH:4][C:3]2[C:2]([CH3:25])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=2[CH:7]=1)=[O:15])[CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 8148DibutylamineHCID 24387Phosphorus trichlorideHCID 9905799HCID 9905799, compound

Product 1

HCID 54231666HCID 54231666, compoundYield 26.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.68 g (5 mmoles) of 2-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl]benzoic acid in 20 cm3 of anhydrous dichloromethane, there is added 0.22cm3 (2.5 mmoles) of phosphorus trichloride. The mixture is heated for 3 hours at reflux. After cooling to +5° C., 2.6 cm3 (15 mmoles) of dibutylamine are added. Stirring is maintained for 30 minutes at +5° C., and then for 1 additional hour so as to permit the reaction mixture to return to ambient temperature. The reaction mixture is then diluted to about 80 cm3 by the addition of dichloromethane. It is then transferred to a decanting ampoule and washed first with diluted HCl and then with water. The dichloromethane phase is dried on sodium sulfate and then concentrated under reduced pressure. The resulting crude product is purified by chromatography on silica 60 gel in a 5/3/2 toluene/dichloromethane/ethyl acetate eluant mixture. After evaporation and drying under a vacuum a 80° C., 0.6 g of N,N-di-n-butyl 2-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) carbonyl]benzamide in the form of a colorless thick oil is obtained. The NMR1H 80 MHz and IR spectra correspond to the expected structure.

Workup

  1. temperatureThe mixture is heated for 3 hours
  2. temperatureat reflux
  3. temperatureAfter cooling to +5° C.
  4. temperatureis maintained for 30 minutes at +5° C.
  5. customto return to ambient temperature
  6. washwashed first with diluted HCl
  7. dry with materialThe dichloromethane phase is dried on sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting crude product is purified by chromatography on silica 60 gel in a 5/3/2 toluene/dichloromethane/ethyl acetate eluant mixture
  10. customAfter evaporation
  11. customdrying under a vacuum a 80° C.

Sources & evidence

ORD record
ord-77d48e4caae84857b1cf699f2809ab6a
Source dataset
uspto-grants-1990_02
Patent number
US04898864

Reaction notes

Loading…