4-Phenylbenzoyl chloride → HCID 21940042, compound

HRID 1242910Notes

Reaction equation

HRID 1242910 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:16][C:17]1[CH:27]=[CH:26][C:20]([CH:21]=[CH:22][C:23]([OH:25])=[O:24])=[CH:19][CH:18]=1.C(=O)([O-])O.[Na+]>O.C(OCC)C>[C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:15]=[CH:14][C:10]([C:11]([NH:16][C:17]2[CH:18]=[CH:19][C:20](/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24])=[CH:26][CH:27]=2)=[O:12])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 841514-Phenylbenzoyl chlorideHCID 929283-(4-Aminophenyl)prop-2-enoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 21940042HCID 21940042, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

4-Phenylbenzoyl chloride (2.00 g, 9.23 mmol) was added to a mixed solution of 4-aminocinnamic acid (1.51 g, 9.23 mmol) and sodium hydrogen carbonate (2.33 g, 27.7 mmol) in water and diethyl ether under ice-cooling, which was stirred for 5 hours. After the reaction mixture was separated, 5N hydrochloric acid was added to water layer, and the precipitated crude product was washed with water and ethyl acetate, to give the titled compound (1.34 g).

Workup

  1. temperaturecooling
  2. customAfter the reaction mixture was separated
  3. addition5N hydrochloric acid was added to water layer
  4. customthe precipitated crude product
  5. washwas washed with water and ethyl acetate

Sources & evidence

ORD record
ord-6a78602f84cb4020b3e69d9ebb560dbf
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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