Triethylamine → HCID 86754924, compound

HRID 610624Notes

Reaction equation

HRID 610624 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([CH2:12][C:13]1[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[N:15]=[CH:16][N:17]=1)[CH2:6][CH2:5]2.C(N(CC)CC)C.[F:34][C:35]([F:52])([F:51])[C:36]1[CH:41]=[CH:40][C:39]([C:42]2[C:43]([C:48](Cl)=[O:49])=[CH:44][CH:45]=[CH:46][CH:47]=2)=[CH:38][CH:37]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][N:14]2[C:13]([CH2:12][N:7]3[CH2:6][CH2:5][C:4]4[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:48]([C:43]5[C:42]([C:39]6[CH:40]=[CH:41][C:36]([C:35]([F:34])([F:51])[F:52])=[CH:37][CH:38]=6)=[CH:47][CH:46]=[CH:45][CH:44]=5)=[O:49])[CH:3]=4)[CH2:8]3)=[N:17][CH:16]=[N:15]2)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 10521771HCID 10521771, compoundHCID 110660004'-(Trifluoromethyl)-[1,1'-biphenyl]-2-carbonyl chloride

Product 1

HCID 86754924HCID 86754924, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The title product of Example 3 (0.38 g, 1.1 mmol) and triethylamine (0.17 mL, 1.2 mmol) were dissolved in methylene chloride (14 mL) and stirred at room temperature while a solution of 4'-trifluoromethylbiphenyl-2-carbonyl chloride (0.31 g, 1.1 mmol) in methylene chloride (40 mL) was added dropwise. After four hours, 10% aq sodium carbonate solution was added and the mixture was stirred for thirty minutes. The methylene chloride layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo to afford the title product as a hard foam, 0.63 g, 97% yield. 1H NMR (CDCl3) δ 7.79 (s, 1), 7.72 (d, 1), 7.64 (d, 2), 7.58-7.34 (m, 6), 7.12 (d, 2), 7.01 (s, 1), 6.90-6.72 (m, 4), 5.38 (s, 2), 3.73 (s, 3), 3.69 (s, 2), 3.50 (s, 2), 2.79 (t, 2), 2.68 (t, 2). IR (KBr) 1668, 1615, 1599, 1567, 1536, 1514 cm-1. Mass spectrum: m/z: 598 (M+ -1).

Workup

  1. additionwas added dropwise
  2. washThe methylene chloride layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-4a0f7116041b4d0bbb6bdc5a2f6f2d48
Source dataset
uspto-grants-1999_12
Patent number
US05998623

Reaction notes

Loading…