1,1'-Carbonyldiimidazole → 2-(t-Butylamino)ethyl 2-phenylbenzofuran-7-carboxylate

HRID 1761915

Reaction equation

HRID 1761915 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=3[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:31]([NH:35][CH2:36][CH2:37]O)([CH3:34])([CH3:33])[CH3:32]>O1CCCC1>[C:1]1([C:7]2[O:8][C:9]3[C:15]([C:16]([O:18][CH2:37][CH2:36][NH:35][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=3[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 783612-(tert-Butylamino)ethanolHCID 142297062-Phenylbenzofuran-7-carboxylic acid

Product 1

HCID 142298072-(t-Butylamino)ethyl 2-phenylbenzofuran-7-carboxylateYield 84.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.43 g of 2-phenylbenzofuran-7-carboxylic acid are dissolved in 10 ml of tetrahydrofuran, and 1.08 g of carbonyldiimidazole are added to the solution. The mixture is stirred at room temperature for 2 hours and a solution of 0.76 g of 2-(t-butylamino)ethanol in 4 ml of tetrahydrofuran is added thereto. The mixture is stirred at room temperature for 15 hours and evaporated to remove solvent. Water is added to the residue and the aqueous mixture is extracted with ethyl acetate. The extract is washed with water, dried, and evaporated to remove solvent to give 1.72 g of 2-(t-butylamino)ethyl 2-phenylbenzofuran-7-carboxylate as pale yellow oil.

Workup

  1. stirringThe mixture is stirred at room temperature for 15 hours
  2. customevaporated
  3. customto remove solvent
  4. additionWater is added to the residue
  5. extractionthe aqueous mixture is extracted with ethyl acetate
  6. washThe extract is washed with water
  7. customdried
  8. customevaporated
  9. customto remove solvent

Sources & evidence

ORD record
ord-1e2808da575d4693abce88953851768c
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Linked notes

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