Acryloyl chloride → HCID 43422996, compound

HRID 526061Notes

Reaction equation

HRID 526061 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C(=O)(O)[O-].[Na+].[C:17](Cl)(=[O:20])[CH:18]=[CH2:19]>O1CCCC1.O.C(OC(=O)C)C>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:17](=[O:20])[CH:18]=[CH2:19])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

7

Reactant 3

HCID 13140Acryloyl chlorideHCID 677684-Fluoro-3-nitroanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 43422996HCID 43422996, compoundYield 74.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

2 g (12.81 mmol) of 4-fluoro-3-nitroaniline and 3.2 g (38.43 mmol) of sodium bicarbonate were diluted in 20 mL of tetrahydrofuran and 5 mL of distilled water, and 1.14 mL (14.09 mmol) of acryloyl chloride was slowly added thereto at 0° C., and stirred for 1 hour. Upon the completion of the reaction, the resulting mixture was diluted with ethylacetate and washed with a saturated aqueous solution of sodium bicarbonate. The organic layer was separated, dried over anhydrous Na2SO4, and filtered and distilled under a reduced pressure to obtain 2 g of the title compound (yield: 74%).

Workup

  1. customUpon the completion of the reaction
  2. washwashed with a saturated aqueous solution of sodium bicarbonate
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-72d7dd971a5a41eaae42f020fb1717e3
Source dataset
uspto-grants-2016_05
Patent number
US09345719B2

Reaction notes

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