Dimethylcarbamoyl Chloride → HCID 11198140, compound

HRID 2227724Notes

Reaction equation

HRID 2227724 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:17]=[CH:16][NH:15][N:14]=3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C1COCC1.[CH3:25][N:26]([CH3:30])[C:27](Cl)=[O:28].C([O-])(O)=O.[Na+]>CCOC(C)=O.C(N(CC)CC)C>[CH3:25][N:26]([CH3:30])[C:27]([N:15]1[CH:16]=[CH:17][C:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][C:5]3[CH:18]=[CH:19][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:12][CH:11]=2)=[N:14]1)=[O:28]

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl Chloride2×HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 178505882HCID 178505882, compound

Product 1

HCID 11198140HCID 11198140, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-[4-(4-fluorophenoxy)phenyl]-1H-pyrazole (467 mg, 1.84 mmol) in 7 mL of THF containing 0.3 mL (2.13 mmol) of triethylamine was treated with 0.3 mL (3.2 mmol) dimethylcarbamyl chloride added via syringe. No reaction was observed at room temperature. An additional 0.3 mL of dimethylcarbamyl chloride was added and the reaction was heated at reflux overnight. The reaction was then added to a saturated aqueous NaHCO3 solution and EtOAc. The aqueous layer was washed with EtOAc and the pooled organic layers were dried (Na2SO4), filtered and concentrated to dryness. Column chromatography (7/3 hexane/EtOAc) afforded 282 mg of the title compound as a yellow oil that solidified on standing, mp 59-63° C. 1H NMR (CDCl3): δ8.15 (d, 1H, J=2.7 Hz), 7.80 (d, 2H, J=8.4 Hz), 7.06-6.88 (m, 6H), 6.62 (d, 1H, J=2.7 Hz), 3.30 (br s, 6H).

Workup

  1. additionadded via syringe
  2. customwas observed at room temperature
  3. temperaturethe reaction was heated
  4. temperatureat reflux overnight
  5. washThe aqueous layer was washed with EtOAc
  6. dry with materialthe pooled organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5aba18bddd404753af5f28da07dd5270
Source dataset
uspto-grants-2002_07
Patent number
US06414011B1

Reaction notes

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