p-Toluenesulfonic acid → HCID 10156183, compound

HRID 413912Notes

Reaction equation

HRID 413912 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[CH2:12]([O:14][C:15](=[O:29])[CH:16]([CH2:20][C:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:17](=O)[CH3:18])[CH3:13].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C.C(Cl)(Cl)Cl>[CH2:12]([O:14][C:15]([C:16]1[CH:20]=[C:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:6]([C:5]2[CH:7]=[CH:8][CH:9]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=2)[C:17]=1[CH3:18])=[O:29])[CH3:13]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 73753-(Trifluoromethyl)anilineHCID 312893Ethyl 2-acetyl-4-oxo-4-phenylbutanoate

Product 1

HCID 10156183HCID 10156183, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

m-Trifluoromethylaniline (5 mmol, 0.8 g), 3-oxo-2-(2-oxo-2-phenyl-ethyl)-butyric acid ethyl ester (5 mmol, 1.2 g), and tosic acid (0.1 g) were combined in ethanol, then heated under reflux. The crude material was resuspended in chloroform and washed with water, then with brine. The organic layer was dried over NaSO4. The solids were separated and the solvents removed under vacuum. The resulting oil was purified over silica gel to yield the named product, 1H-NMR (CDCl3, ppm): 1.37 t (3H), 2.42 s (3H), 4.32 q (2H), 6.80 s (1H), 7.0-7.6 bm (9H).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. washwashed with water
  4. dry with materialThe organic layer was dried over NaSO4
  5. customThe solids were separated
  6. customthe solvents removed under vacuum
  7. customThe resulting oil was purified over silica gel
  8. customto yield the named product, 1H-NMR (CDCl3, ppm): 1.37 t (3H), 2.42 s (3H), 4.32 q (2H), 6.80 s (1H), 7.0-7.6 bm (9H)

Sources & evidence

ORD record
ord-4bc6f6b4c4bb40ddaff09e1b934e98c0
Source dataset
uspto-grants-2003_05
Patent number
US06569890B2

Reaction notes

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