1(3H)-Isobenzofuranone, 3-bromo- → Phthalidyl 2-(2,6-dichloroanilino)-phenylacetate

HRID 371113Notes

Reaction equation

HRID 371113 reaction equation
Br[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[O:3]1.[Cl:12][C:13]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:14]=1[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][C:23]([O-:25])=[O:24].[Na+]>CN(C)C=O>[Cl:12][C:13]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:14]=1[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][C:23]([O:25][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[O:3]1)=[O:24]

Participants

4

Reactant 2

HCID 962181(3H)-Isobenzofuranone, 3-bromo-HCID 5018304Diclofenac sodium

Product 1

HCID 12769706Phthalidyl 2-(2,6-dichloroanilino)-phenylacetateYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 10.65 g of 3-bromophthalide in 120 ml of dimethylformamide at room temperature is added 15.9 g of sodium 2-(2,6-dichloroanilino)-phenylacetate. The reaction mixture is stirred 24 hours at the room temperature, and then poured into 500 ml of ice water. After extraction with chloroform, the aqueous phase is washed with an aqueous solution of sodium bicarbonate, then with water and finally it is dried on anhydrous sodium sulfate and evaporated to dryness to yield the phthalidyl 2-(2,6-dichloroanilino)-phenylacetate; yield 70%.

Workup

  1. extractionAfter extraction with chloroform
  2. washthe aqueous phase is washed with an aqueous solution of sodium bicarbonate
  3. dry with materialwith water and finally it is dried on anhydrous sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-71bce0621b25496caee906fa3f8a042c
Source dataset
uspto-grants-1985_07
Patent number
US04529737

Reaction notes

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