4-Ethylbenzoic Acid → HCID 59238224, compound

HRID 1359913Notes

Reaction equation

HRID 1359913 reaction equation
P(Cl)(Cl)(Cl)=O.[Sn](Cl)(Cl)(Cl)Cl.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:14][C:13]=1[O:22][CH3:23].[CH2:24]([C:26]1[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=1)[CH3:25]>ClCCCl.ClCCl>[Br:11][C:12]1[C:13]([O:22][CH3:23])=[CH:14][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[C:16]([C:30](=[O:31])[C:29]2[CH:33]=[CH:34][C:26]([CH2:24][CH3:25])=[CH:27][CH:28]=2)[CH:17]=1

Participants

7

Reactant 4

HCID 120864-Ethylbenzoic AcidHCID 24287Tin tetrachlorideHCID 24813Phosphorus oxychlorideHCID 59238262HCID 59238262, compound

Product 1

HCID 59238224HCID 59238224, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Phosphorus oxychloride (17 mL) and tin(IV) chloride (5 mL) are successively added to a suspension of N-(4-bromo-3-methoxy-phenyl)-acetamide (5.0 g) and 4-ethylbenzoic acid (4.4 g) in 1,2-dichloroethane at such a rate that the temperature maintains below 35° C. The resulting mixture is heated at reflux temperature overnight. Then, the mixture is diluted with dichloromethane and poured onto crushed ice. After stirring the aqueous mixture for 30 min, the organic phase is separated and washed with 10% NaOH in water and water. The organic phase is dried (sodium sulphate), the solvent is removed and the residue is triturated with methanol to give the product.

Workup

  1. custommaintains below 35° C
  2. temperatureThe resulting mixture is heated
  3. temperatureat reflux temperature overnight
  4. additionpoured
  5. customonto crushed ice
  6. customthe organic phase is separated
  7. washwashed with 10% NaOH in water and water
  8. dry with materialThe organic phase is dried (sodium sulphate)
  9. customthe solvent is removed
  10. customthe residue is triturated with methanol
  11. customto give the product

Sources & evidence

ORD record
ord-1a0a2b17053d4c2fb5c8aa281c3d0ea5
Source dataset
uspto-grants-2011_02
Patent number
US07879806B2

Reaction notes

Loading…