Triethylamine → HCID 22054335, compound

HRID 1830348Notes

Reaction equation

HRID 1830348 reaction equation
[Cl-].ClC1N(C)CC[NH+]1C.[F:10][C:11]([F:23])([F:22])[S:12]([C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13].C(N(CC)CC)C.[CH3:31][O:32][C:33]1[C:34](=[O:57])[C:35]([CH3:56])=[C:36]([CH2:42][C:43]2[CH:51]=[CH:50][C:46]([C:47](O)=[O:48])=[C:45]([O:52][C:53](=[O:55])[CH3:54])[CH:44]=2)[C:37](=[O:41])[C:38]=1[O:39][CH3:40]>C(Cl)(Cl)Cl.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[CH:51]=[CH:50][C:46]([C:47]([NH:19][C:18]3[CH:20]=[CH:21][C:15]([S:12]([C:11]([F:22])([F:10])[F:23])(=[O:13])=[O:14])=[CH:16][CH:17]=3)=[O:48])=[C:45]([O:52][C:53](=[O:55])[CH3:54])[CH:44]=2)[C:37](=[O:41])[C:38]=1[O:39][CH3:40]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 1363154-Aminophenyl trifluoromethyl sulphoneHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 22054194HCID 22054194, compound

Product 1

HCID 22054335HCID 22054335, compoundYield 39.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

2-Chloro-1,3-dimethylimidazolinium chloride (130 mg, 0.77 mmol), 4-(trifluoromethylsulfonyl)aniline (173 mg, 0.77 mmol) and triethylamine (78 mg, 0.77 mmol) were added to a methylene chloride solution (8 ml) of 4-[(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl]-2-acetoxybenzoic acid (240 mg, 0.64 mmol) in a nitrogen atmosphere and the resulting solution was stirred for 2 hours. The reaction solution was diluted with chloroform, then washed with water and dried, and the solvent was removed by distillation. The residue was purified by silica gel column chromatography (methylene chloride:methanol=60:1) to obtain the titled compound (146 mg, 0.251 mmol, 39%).

Workup

  1. washwashed with water
  2. customdried
  3. customthe solvent was removed by distillation
  4. customThe residue was purified by silica gel column chromatography (methylene chloride:methanol=60:1)

Sources & evidence

ORD record
ord-3cef56cab2e649bdb37e0cf054145f9a
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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