Triethylamine → HCID 15462010, compound

HRID 1003738Notes

Reaction equation

HRID 1003738 reaction equation
[N+:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[C-:2].C(N(CC)CC)C.[F:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[F:25])[C:19](Cl)=[O:20]>C1COCC1>[F:15][C:16]1[CH:17]=[C:18]([C:19]2[O:20][CH:2]=[N:1][C:3]=2[C:4]([O:6][CH3:7])=[O:5])[CH:22]=[CH:23][C:24]=1[F:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 547815Methyl isocyanoacetateHCID 27245193,4-Difluorobenzoyl chloride

Product 1

HCID 15462010HCID 15462010, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a well stirred solution of the methyl isocyanoacetate (2 g, 20.2 mmol) in THF (3 mL), triethyl amine (8.4 mL, 6.06 mmol) was added and the reaction mixture was stirred for 15 minutes. Then 3,4-difluorobenzoylchloride (2.5 mL, 20.20 mmol) was added neat over a period of five minutes and the reaction mixture was allowed to stir at room temperature for 48 hours. It was then concentrated, partitioned between ethyl acetate (50 mL) and water. The organic layer was washed with 10% NaOH solution (20 mL), dried over sodium sulfate, filtered and concentrated to yield 3.8 g (79%) of a brown solid which was recrystallized from hexanes: 1H-NMR (CDCl3) δ3.74(s, 3H), 7.47-7.50 (m, 1 H), 7.92 (s, 2 H), 8.01-8.10 (m, 2 H).

Workup

  1. stirringto stir at room temperature for 48 hours
  2. concentrationIt was then concentrated
  3. custompartitioned between ethyl acetate (50 mL) and water
  4. washThe organic layer was washed with 10% NaOH solution (20 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c7aa0a8988694fcdb567e76f06bbcf1b
Source dataset
uspto-grants-2000_04
Patent number
US06046331

Reaction notes

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