Triethylamine → N-(4-Benzoyl-2-cyanophenyl)-3,3,3,-trifluoro-2-hydroxy-2-methylpropanamide

HRID 374881Notes

Reaction equation

HRID 374881 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([OH:8])([CH3:7])[C:4](O)=[O:5].S(Cl)(Cl)=O.C(N(CC)CC)C.[C:22]([C:24]1[CH:25]=[C:26]([CH:35]=[CH:36][C:37]=1[NH2:38])[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:28])#[N:23]>C(Cl)Cl.O1CCCC1.C(OCC)C>[C:27]([C:26]1[CH:35]=[CH:36][C:37]([NH:38][C:4](=[O:5])[C:3]([OH:8])([CH3:7])[C:2]([F:10])([F:9])[F:1])=[C:24]([C:22]#[N:23])[CH:25]=1)(=[O:28])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acidHCID 107753914-Amino-3-cyanobenzophenone

Product 1

HCID 9950829N-(4-Benzoyl-2-cyanophenyl)-3,3,3,-trifluoro-2-hydroxy-2-methylpropanamideYield 35.5%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred, cooled solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (0.15 g) in methylene chloride (10 mL) was added thionyl chloride (0.12 g) and the mixture was stirred at reflux for 3 hours. The mixture was cooled to room temperature, triethylamine (0.11 g) added and the mixture stirred at reflux for 0.5 hour. The mixture was again cooled to room temperature, 3-cyano-4-aminobenzophenone (0.19 g) in tetrahydrofuran (2.5 mL) was added and the mixture stirred at reflux overnight. The solvent was evaporated and the residue portioned between ethyl acetate and 3N HCl. The organic layer was washed with water, dried and evaporated to yield a pale yellow oil. Chromatography (eluent methylene chloride then 2% ethyl ether in methylene chloride) gave the title compound (0.11 g) as a white solid; mp 202°-204° C. Analysis for C18H13F3N2O3.0.5 H2O: Calculated: C, 58.22; H, 3.80; N, 7,54; Found: C, 58.03; H, 3.57; N, 7.26.

Workup

  1. temperatureat reflux for 3 hours
  2. stirringthe mixture stirred
  3. temperatureat reflux for 0.5 hour
  4. temperatureThe mixture was again cooled to room temperature
  5. stirringthe mixture stirred
  6. temperatureat reflux overnight
  7. customThe solvent was evaporated
  8. washThe organic layer was washed with water
  9. customdried
  10. customevaporated
  11. customto yield a pale yellow oil

Sources & evidence

ORD record
ord-bf01497472df4e0988df35ad36ae930b
Source dataset
uspto-grants-1996_01
Patent number
US05482969

Reaction notes

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