Triethylamine → HCID 22054215, compound

HRID 1830389Notes

Reaction equation

HRID 1830389 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl-].ClC1N(C)CC[NH+]1C.[CH3:30][O:31][C:32]1[C:33](=[O:56])[C:34]([CH3:55])=[C:35]([CH2:41][C:42]2[C:43]([O:51][C:52](=[O:54])[CH3:53])=[C:44]([CH:48]=[CH:49][CH:50]=2)[C:45](O)=[O:46])[C:36](=[O:40])[C:37]=1[O:38][CH3:39]>C(Cl)Cl>[CH3:30][O:31][C:32]1[C:33](=[O:56])[C:34]([CH3:55])=[C:35]([CH2:41][C:42]2[C:43]([O:51][C:52](=[O:54])[CH3:53])=[C:44]([CH:48]=[CH:49][CH:50]=2)[C:45]([NH:11][C:10]2[CH:12]=[CH:13][C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)=[CH:8][CH:9]=2)=[O:46])[C:36](=[O:40])[C:37]=1[O:38][CH3:39]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 22054160HCID 22054160, compound

Product 1

HCID 22054215HCID 22054215, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Morpholinoaniline (0.214 g, 1.203 mmol), triethylamine (0.122 g, 1.203 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (0.203 g, 1.203 mmol) were added to a methylene chloride solution (40 ml) of 3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (0.150 g, 0.401 mmol) and the resulting solution was stirred at room temperature for 10 hours. The reaction solution was poured into ice water and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (ethyl acetate) and then recrystallized from ether to obtain the titled compound (0.109 g, 0.203 mmol, 51%).

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was removed by distillation
  5. customThe obtained residue was purified by preparative thin-layer chromatography (ethyl acetate)
  6. customrecrystallized from ether

Sources & evidence

ORD record
ord-c6fde6b4753c4d78b4c19fdd9480099e
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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