Hydrochloric Acid → HCID 70236392, compound

HRID 566173Notes

Reaction equation

HRID 566173 reaction equation
Cl.[NH2:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1.[F:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1.Cl>CC(N(C)C)=O.N1C=CC=CC=1>[F:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([C:8](=[CH:7][C:6]2[CH:5]=[CH:4][C:3]([NH2:2])=[CH:13][CH:12]=2)[C:9]([OH:11])=[O:10])=[O:20])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 678794-Fluorobenzoyl chlorideHCID 1038662-Propenoic acid, 3-(4-aminophenyl)-, hydrochloride

Product 1

HCID 70236392HCID 70236392, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Procedure

Para-aminocinnamic acid hydrochloride (0.1 mol, 19.96 g) was dissolved in 100 milliliters (ml) of dimethylacetamide and 30 ml pyridine, then 0.1 mol of para-fluorobenzoylchloride was added dropwise while the solution was maintained at 0° C. The solution was allowed to react for about 5 hours at room temperature, and then neutralized to a pH of 6 to 7 with hydrochloric acid. The solution was filtered to obtain a reaction intermediate. The intermediate was washed with water, dried under a vacuum and recrystallized in a solution of dimethylacetamide (10%) and water (90%). A yield of 90% N (para-fluorbenzoyl)-para-aminocinnamic acid in was obtained. Thionyl chloride (1.2 equivalents) and 50 ml of methylene chloride were added. The solution was allowed to react until clear. After the reaction, the solvent and thionyl chloride were removed under a vacuum, and the remaining product was dried. N-(para-fluorbenzoyl)- para-aminocinnamic acid was obtained.

Workup

  1. customto react for about 5 hours at room temperature
  2. filtrationThe solution was filtered
  3. customto obtain a reaction intermediate
  4. washThe intermediate was washed with water
  5. customdried under a vacuum
  6. customrecrystallized in a solution of dimethylacetamide (10%) and water (90%)

Sources & evidence

ORD record
ord-e804d111debf4eb8beb6c1204b8a73a8
Source dataset
uspto-grants-2001_01
Patent number
US06174649B1

Reaction notes

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