Triethylamine → HCID 22054134, compound

HRID 1830386Notes

Reaction equation

HRID 1830386 reaction equation
[F:1][C:2]([F:14])([F:13])[S:3]([C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1)(=[O:5])=[O:4].C(N(CC)CC)C.[Cl-].ClC1N(C)CC[NH+]1C.[CH3:31][O:32][C:33]1[C:34](=[O:57])[C:35]([CH3:56])=[C:36]([CH2:42][C:43]2[C:44]([O:52][C:53](=[O:55])[CH3:54])=[C:45]([CH:49]=[CH:50][CH:51]=2)[C:46](O)=[O:47])[C:37](=[O:41])[C:38]=1[O:39][CH3:40]>C(Cl)Cl>[CH3:31][O:32][C:33]1[C:34](=[O:57])[C:35]([CH3:56])=[C:36]([CH2:42][C:43]2[C:44]([O:52][C:53](=[O:55])[CH3:54])=[C:45]([CH:49]=[CH:50][CH:51]=2)[C:46]([NH:10][C:9]2[CH:11]=[CH:12][C:6]([S:3]([C:2]([F:13])([F:1])[F:14])(=[O:4])=[O:5])=[CH:7][CH:8]=2)=[O:47])[C:37](=[O:41])[C:38]=1[O:39][CH3:40]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1363154-Aminophenyl trifluoromethyl sulphoneHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 22054160HCID 22054160, compound

Product 1

HCID 22054134HCID 22054134, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(Trifluoromethylsulfonyl)aniline (0.361 g, 1.604 mmol), triethylamine (0.162 g, 1.604 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (0.271 g, 1.604 mmol) were added to a methylene chloride solution (50 ml) of 3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (0.200 g, 0.535 mmol) and the resulting solution was stirred at room temperature for 12 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 (chloroform:methanol=10:1) and then recrystallized from ether to obtain the titled compound (0.084 g, 0.144 mmol, 27%).

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 (chloroform:methanol=10:1)
  6. customrecrystallized from ether

Sources & evidence

ORD record
ord-072695272d1e45fa8fb2b64d19c2cd13
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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