Triethylamine → HCID 21082442, compound

HRID 347288Notes

Reaction equation

HRID 347288 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([CH3:13])[CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(N(CC)CC)C.[F:27][C:28]([F:39])([F:38])[C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=O)=[CH:31][CH:30]=1>O1CCCC1>[F:27][C:28]([F:38])([F:39])[C:29]1[CH:30]=[CH:31][C:32]([C:33]2[O:5][C:4](=[O:6])[C:3]3[CH:7]=[C:8]([C:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)([CH3:13])[CH3:12])[CH:9]=[CH:10][C:2]=3[N:1]=2)=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 21082444HCID 21082444, compound

Product 1

HCID 21082442HCID 21082442, compoundYield 7.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-5-α-cumylbenzoic acid (13.5 g, 0.53 mol, prepared in Example 20) and triethylamine (7.8 g, 0.56 mol) in tetrahydrofuran (200 mL) is added dropwise at room temperature a solution of 4-trifluoromethylbenzoyl chloride (11 g, 0.53 mol). The resulting suspension is stirred at room temperature overnight, then filtered and concentrated to a solid that is then suspended in acetic anhydride and heated to 115° C. for three hours. The resulting solution is cooled and concentrated to an oil. The oil is taken up in ethanol (100 mL) and allowed to stand. The resulting solid formed is coiled and dried to give 15.4 g of the title compound melting at 104–105° C. The structure of the compound is confirmed by 1Hnmr (CDCl3) 500 MHz: δ 1.78 (s, 6H); 7.23 (t, 1H); 7.23 (d, 2H); 7.31 (t, 2H); 7.60 (d, 1H); 7.64 (dd, 1H); 7.78 (d, 2H); 8.26 (d, 1H). 19Fnmr (fluorinated species at −69.57 ppm).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to a solid
  3. temperatureheated to 115° C. for three hours
  4. temperatureThe resulting solution is cooled
  5. concentrationconcentrated to an oil
  6. customThe resulting solid formed
  7. customdried

Sources & evidence

ORD record
ord-5aa363b0c65c40e8b85bcbab21fcb5b1
Source dataset
uspto-grants-2007_02
Patent number
US07173128B2

Reaction notes

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