Diethylamine → HCID 18545673, compound

HRID 1267505Notes

Reaction equation

HRID 1267505 reaction equation
F[C:2]1C=C(C=CC=1)N.C(C1C=CC(C(O)=O)=CC=1)(=O)C1C=CC=CC=1.C(NCC)C.[F:31][C:32]1[CH:33]=[C:34]([NH:38][C:39](=[O:54])[C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([C:46](=[O:53])[C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[CH:41]=2)[CH:35]=[CH:36][CH:37]=1.[H-].[Na+]>C1COCC1>[F:31][C:32]1[CH:33]=[C:34]([N:38]([CH3:2])[C:39](=[O:54])[C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([C:46](=[O:53])[C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[CH:41]=2)[CH:35]=[CH:36][CH:37]=1

Participants

7

Reactant 5

HCID 8021DiethylamineHCID 97423-FluoroanilineHCID 24758Sodium hydrideHCID 691474-Benzoylbenzoic acidHCID 18545706HCID 18545706, compound

Product 1

HCID 18545673HCID 18545673, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Following Procedure A with the substitution of 20 g (88 mmol) 3-benzoylbenzoic acid [579-18-0] and 8.5 mL (88 mmol) 3-fluoroaniline for 4-benzoylbenzoic acid and diethyl amine, the product N-(3-fluorophenyl)-3-benzoylbenzamide was generated (28 g, 88 mmol) as a clear oil. The oil was dissolved in 50 mL dry THF to which a 10 mL THF slurry of 2.1 g (90 mmol) NaH was slowly added. The mixture was allowed to stir for 5 min then 5.6 mL (90 mmol) of Mel was added and continued stirring for 16 h. The reaction was carefully quenched with water and partitioned between water and CH2Cl2. The organic layer was washed with brine, dried over K2CO3, filtered, and concentrated to yield 29.3 g (88 mmol) product. MS m/z (MH+) 334.

Workup

  1. additionwas slowly added
  2. addition5.6 mL (90 mmol) of Mel was added
  3. stirringcontinued stirring for 16 h
  4. customThe reaction was carefully quenched with water
  5. custompartitioned between water and CH2Cl2
  6. washThe organic layer was washed with brine
  7. dry with materialdried over K2CO3
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c72f885c3a674656a06705aa63a0e5df
Source dataset
uspto-grants-2003_04
Patent number
US06552036B2

Reaction notes

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