Hydrochloric Acid → HCID 11608550, compound

HRID 1256888Notes

Reaction equation

HRID 1256888 reaction equation
[CH3:1][NH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>C1COCC1.[OH-].[Na+]>[C:12]([N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 663454-(Methylamino)benzoic acid

Product 1

HCID 11608550HCID 11608550, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a mixture of 4-(methylamino)benzoic acid (1.50 g) in THF (30 mL) and 1 mol/L aqueous sodium hydroxide solution (30 mL) was added dropwise benzoyl chloride (1.20 mL) under ice-cooling, and the mixture was stirred at room temperature for 14 hr. The reaction mixture was adjusted to pH=1-2 by the addition of dilute hydrochloric acid, and extracted with ethyl acetate (50 mL×2). The organic layer was washed with saturated brine and concentrated under reduced pressure. The residue was washed with a chloroform/hexane mixture and collected by filtration to give the title compound (1.81 g) as a white solid.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate (50 mL×2)
  3. washThe organic layer was washed with saturated brine
  4. concentrationconcentrated under reduced pressure
  5. washThe residue was washed with a chloroform/hexane mixture
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-63a2b4b45cd34a76988f1ad28342f7b6
Source dataset
uspto-grants-2013_06
Patent number
US08461209B2

Reaction notes

Loading…