Hydrochloric Acid → N-(8-phenyl-octyl)-3,5-bis(m-trifluoromethylphenyl)4hydroxy-benzamide

HRID 1281450Notes

Reaction equation

HRID 1281450 reaction equation
C(O[C:4](=[O:32])[C:5]1[CH:10]=[C:9](C2C=CC=C(C(F)(F)F)C=2)[C:8]([OH:21])=[C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[CH:6]=1)C.S(Cl)(Cl)=O.[C:37]1(NCCCCCCCC)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C([N:54]([CH2:57][CH3:58])CC)C.Cl>>[C:7]1([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:58][CH2:57][NH:54][C:4]([C:5]2[CH:10]=[C:9]([C:41]3[CH:40]=[CH:39][CH:38]=[C:37]([C:28]([F:29])([F:30])[F:31])[CH:42]=3)[C:8]([OH:21])=[C:7]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:29])([F:30])[F:31])[CH:23]=3)[CH:6]=2)=[O:32])[CH:8]=[CH:9][CH:10]=[CH:5][CH:6]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 137788N-OctylanilineHCID 538160993,5-Bis-(m-trifluoromethylphenyl)-4-hydroxy-benzoic acid ethyl ester

Product 1

HCID 22237600N-(8-phenyl-octyl)-3,5-bis(m-trifluoromethylphenyl)4hydroxy-benzamideYield 173.1%

Procedure

To 3,5-bis-(m-trifluoromethylphenyl)-4-hydroxy-benzoic acid ethyl ester (0.315 g, 0.74 mmol, 1 eq) was added thionyl chloride (2 mL) and the reaction was stirred overnight at rt and concentrated in vacuo. It was then added to a solution of phenyl octyl amine (0.222 mL, 1.12 mmol, 1 .51 eq) and triethylamine (0.470 mL, 3.37 mmol, 4.6 eq). The reaction was stirred at rt lh, poured into 0.1 N HCl solution and extracted with Et2O. The combined organics were washed with 1N HCl (×3), dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (20% EtOAc:hexane) to afford title compound (0.393 g, 86%) as a colorless oil. 1H NMR (DMSO-d6) δ 9.30 (s, 1H); 8.42 (t, 1H); 7.91-7.85 (m, 4H); 7.82 (s, 2H); 7.75-7.65 (m, 4H); 7.26-7.10 (m, 5H); 3.23 (dd, 2H); 2.52 (t, 2H); 1.52 (m, 4H); 1.27 (m, 8H); IR (film) 3330, 2980, 2840, 1640, 1600, 1550, 1470, 1320, 1180, 1120, 1080, 900, 805 cm−1; mass spectrum [(+)APCI], m/z 614 (M+H)+; Anal. Calcd. for C35H33F6NO2: C, 68.51; H, 5.42; N, 2.28, Found: C, 66.76; H, 5.46; N, 2.18.

Workup

  1. concentrationconcentrated in vacuo
  2. stirringThe reaction was stirred at rt lh
  3. extractionextracted with Et2O
  4. washThe combined organics were washed with 1N HCl (×3)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (20% EtOAc:hexane)

Sources & evidence

ORD record
ord-b5689365e692452b9f26fe23f0bba94e
Source dataset
uspto-grants-2002_09
Patent number
US06451827B2

Reaction notes

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