Water → HCID 68523174, compound

HRID 884109Notes

Reaction equation

HRID 884109 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5](Cl)=[O:6].[NH2:12][C:13]1[CH:32]=[CH:31][C:16]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20][CH:19]=2)=[CH:15][CH:14]=1.C(N(CC)CC)C.O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20][CH:19]=2)=[CH:31][CH:32]=1)=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 68523825HCID 68523825, compound

Product 1

HCID 68523174HCID 68523174, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3,4-dichlorobenzoyl chloride (3.65 g, 17.4 mmol) was added dropwise under ice cooling to a solution of ethyl 3-[4-(4-aminophenoxy)phenyl]propionate (4.52 g, 15.9 mmol) and triethylamine (2.65 mL, 19.0 mmol) in THF (80 mL), and the resulting solution was stirred for 1 hour at the same temperature. Water was added to the reaction mixture, and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine. The ethyl acetate layer was dried over anhydrous magnesium sulfate and evaporated. The residue was recrystallized from water-containing ethanol to thereby yield 6.67 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine
  3. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was recrystallized from water-
  6. additioncontaining ethanol to thereby yield 6.67 g of the title compound

Sources & evidence

ORD record
ord-6d25d0bce69d446f86573e01a583298f
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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