Hydrochloric Acid → HCID 118324065, compound

HRID 1778212Notes

Reaction equation

HRID 1778212 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:22])[CH2:16][C:17]([O:19]CC)=[O:18])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.CCO.[OH-].[K+].Cl>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:22])[CH2:16][C:17]([OH:19])=[O:18])=[CH:12][CH:13]=2)=[O:7])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium Hydroxide2×HCID 118324030HCID 118324030, compound

Product 1

HCID 118324065HCID 118324065, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A 3-L 4-neck flask equipped with a thermocouple controller, a mechanical stirrer, a dropping funnel, and a nitrogen inlet/outlet adapter was charged with ethyl 3-((4-(4-chlorobenzoyl)phenyl)amino)-3-oxopropanoate (128.0 g, 370.2 mmol), EtOH (1.29 L), and KOH (27.7 g, 1444.2 mmol). The resulting mixture was stirred at 20° C. for 24 h. Additional KOH (1.12 g, 0.04 eq.) was added and the reaction was stirred for an additional 6 h. The resulting yellowish thick slurry was dissolved in deionized water (1.2 L) and then poured into a 12-L 4-neck flask equipped with an overhead stirrer that contained ice-water (6 L) in an ice-water bath. The aqueous pH was adjusted to pH 2-3 using 2 N aqueous HCl solution with fast stirring at 8-10° C. for 20 min. The solid in the resulting milky slurry was collected by filtration, washed with deionized water (100 mL), dried under air-suction for 20 h and then in a vacuum oven at 60° C. under hi-vacuum (20 mmHg) for 72 h to yield 3-((4-(4-chlorobenzoyl)phenyl)amino)-3-oxopropanoic acid as a yellowish solid, which was used in the next step without further purification. (ES, m/z) 318, 320 (M+H)+

Workup

  1. customA 3-L 4-neck flask equipped with a thermocouple controller, a mechanical stirrer, a dropping funnel, and a nitrogen inlet/outlet adapter
  2. stirringthe reaction was stirred for an additional 6 h
  3. additionpoured into a 12-L 4-neck flask
  4. customequipped with an overhead stirrer that
  5. stirringwith fast stirring at 8-10° C. for 20 min
  6. filtrationThe solid in the resulting milky slurry was collected by filtration
  7. washwashed with deionized water (100 mL)
  8. customdried under air-suction for 20 h

Sources & evidence

ORD record
ord-2841a5dff20a498a9416806cebce5a48
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

Loading…