Dichloromethane → HCID 15239200, compound

HRID 861563Notes

Reaction equation

HRID 861563 reaction equation
[F:1][C:2](=[C:7]([F:9])[F:8])[CH2:3][C:4](Cl)=[O:5].[NH2:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([OH:16])=[O:15].C(=O)(O)[O-].[Na+].ClCCl>C(OCC)(=O)C.O>[F:1][C:2](=[C:7]([F:9])[F:8])[CH2:3][C:4]([NH:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([OH:16])=[O:15])=[O:5]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 74193-Aminobenzoic AcidHCID 516892Sodium BicarbonateHCID 109207893,4,4-Trifluoro-3-butenoyl chloride

Product 1

HCID 15239200HCID 15239200, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

2.2 g (0.0139 mole) 3,4,4-trifluoro-3-butenoyl chloride is added to a mixture of 3-aminobenzoic acid (1.37 g, 0.01 mole), sodium bicarbonate (0.84 g, 0.01 mole), water (20 mL) and dichloromethane (20 mL) with stirring at 0° C. After stirring for 15 min at room temperature, the mixture is diluted with ethyl acetate (100 mL) and water (50 mL). The organic layer is washed with 2N HCl and brine, and dried. The residue obtained after evaporation of the solvent is triturated with dry ether and filtered to give 1.8 g of the title compound as a light pink solid, a 69% yield. m.p. 252°-255° C.

Workup

  1. stirringAfter stirring for 15 min at room temperature
  2. washThe organic layer is washed with 2N HCl and brine
  3. customdried
  4. customThe residue obtained
  5. customafter evaporation of the solvent
  6. customis triturated with dry ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-5c3c8f864fd445f8b836dbd2ebc3e125
Source dataset
uspto-grants-1998_02
Patent number
US05714517

Reaction notes

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