Triethylamine → HCID 54197126, compound

HRID 1588921Notes

Reaction equation

HRID 1588921 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:11][CH3:12].[CH:13]([NH:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)([CH3:15])[CH3:14].C(N(CC)CC)C>S(Cl)(Cl)=O.C1COCC1>[CH:13]([N:16]([CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[C:3]([O:11][CH3:12])[CH:4]=1)([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62386CyclohexylisopropylamineHCID 162158674-Bromo-3-methoxybenzoic acid

Product 1

HCID 54197126HCID 54197126, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 4-bromo-3-methoxybenzoic acid (2.80 g, 12.1 mmol) in thionyl chloride (30 mL) was refluxed for 3 hr. The reaction was concentrated in vacuo and the residue azeotroped three times with toluene. A solution of the resulting crude solid (3.11 g, 8.75 mmol) in THF (10 mL) was added to a stirred, cold (0° C.) solution of N-isopropylcyclohexyl amine (1.7 g, 11.7 mmol) and triethylamine (1.20 g, 11.7 mmol) in THF (10 mL). The reaction was stirred at room temperature overnight. The reaction was filtered and the filtrate diluted with ethyl acetate and washed three times with 1N HCl, three times with saturated NaHCO3, three times with saturated NaCl solution and dried (Na2SO4). The drying agent was filtered and the filtrate concentrated in vacuo to give a dark brown oil. The oil was purified by chromatography on silica gel using mixtures of ethyl acetate and hexane as eluents. This yielded crystalline amide, m. p. 104-107° C.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue azeotroped three times with toluene
  3. filtrationThe reaction was filtered
  4. additionthe filtrate diluted with ethyl acetate
  5. washwashed three times with 1N HCl, three times with saturated NaHCO3, three times with saturated NaCl solution
  6. dry with materialdried (Na2SO4)
  7. filtrationThe drying agent was filtered
  8. concentrationthe filtrate concentrated in vacuo
  9. customto give a dark brown oil
  10. customThe oil was purified by chromatography on silica gel using mixtures of ethyl acetate and hexane as eluents

Sources & evidence

ORD record
ord-d58b798cf5cf46c4941b12ebde306104
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

Loading…