Sodium Carbonate → HCID 2781632, compound

HRID 550156Notes

Reaction equation

HRID 550156 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[F:7][C:8]([F:18])([F:17])[O:9][C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12].C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>O>[F:7][C:8]([F:17])([F:18])[O:9][C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH:12][C:2](=[O:3])[O:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 10928Ethyl chloroformateHCID 312751,4-DioxaneHCID 737542-(Trifluoromethoxy)aniline

Product 1

HCID 2781632HCID 2781632, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl chloroformate (4.4 mL, 0.046 mol) was added to a mixture of 2-(trifluoromethoxy)aniline (8.25 g, 0.0466 mol), sodium carbonate (15 g, 0.14 mol), 1,4-dioxane (70 mL) and water (70 mL) at 0° C. and the the reaction mixture stirred at room temperature overnight. The reaction mixture was then washed with ether, acidified (pH 3) and the product extracted into EtOAc (3×40 mL). The combined extracts were washed with water (40 mL) and brine (40 mL), dried over Na2SO4 and the solvent removed in vacuo to give the desired product in a 84% yield. 1H NMR (400 MHz, CDCl3): δ 1.33 (t, J=5.2 Hz, 3H), 4.25 (q, J=6.8 Hz, 2H), 6.91 (br, 1H), 7.04 (m, 1H), 7.23 (m, 1H), 7.28 (m, 1H) and 8.2 (m, 1H). MS (ES+): m/z 250.12 [MH+].

Workup

  1. washThe reaction mixture was then washed with ether
  2. extractionthe product extracted into EtOAc (3×40 mL)
  3. washThe combined extracts were washed with water (40 mL) and brine (40 mL)
  4. dry with materialdried over Na2SO4
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-f1055bb1c75c418c806d22098016bae4
Source dataset
uspto-grants-2011_05
Patent number
US07943767B2

Reaction notes

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