Sodium hydride → HCID 68791830, compound

HRID 505871Notes

Reaction equation

HRID 505871 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH3:14])=[CH:8][CH:7]=1)[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:28][S:29]([C:32]1[CH:40]=[CH:39][C:35]([C:36](O)=[O:37])=[CH:34][CH:33]=1)(=[O:31])=[O:30].[H-].[Na+]>CN(C)C=O.O>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH3:14])=[CH:8][CH:7]=1)[C:36](=[O:37])[C:35]1[CH:34]=[CH:33][C:32]([S:29]([CH3:28])(=[O:31])=[O:30])=[CH:40][CH:39]=1)[CH3:2]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 77670p-(Methylsulphonyl)benzoic acidHCID 181675Ethyl 4-ethoxyphenylacetate

Product 1

HCID 68791830HCID 68791830, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

499 mg of 4-ethoxyphenylacetic acid ethyl ester, 480 mg of carbonyldiimidazole, and 0.5 g of 4-methanesulfonyl benzoic acid were dissolved in 10 ml of dimethy formamide, and 119 mg of sodium hydride were slowly added dropwise to the solution and the mixture was reacted at the room temperature for 12 hours. Afterwards, water was added to dilute the resultant, followed by extraction with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate to give 0.9 g of the titled compound as a light yellow liquid (yield 92%).

Workup

  1. customthe mixture was reacted at the room temperature for 12 hours
  2. additionto dilute the resultant
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-16b7f3a7e8ad4b8c8f59fdbe926c5a46
Source dataset
uspto-grants-2010_08
Patent number
US07781592B2

Reaction notes

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