Ethyl bromoacetate → HCID 13476640, compound

HRID 1285385Notes

Reaction equation

HRID 1285385 reaction equation
[CH3:1][C:2]1[C:9]2[CH:8]=[C:7]([C:10](=[O:17])[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:6][C:5]=2[S:4][CH:3]=1.[O-]CC.[Na+].[Na].Br[CH2:24][C:25]([O:27]CC)=[O:26].[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[C:9]2[CH:8]=[C:7]([C:10](=[O:17])[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:6]([CH2:24][C:25]([OH:27])=[O:26])[C:5]=2[S:4][CH:3]=1

Participants

7

Reactant 5

HCID 7748Ethyl bromoacetateHCID 14798Sodium HydroxideHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 13476639HCID 13476639, compound

Product 1

HCID 13476640HCID 13476640, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The previously obtained 3-methyl-5-benzoyl thieno[2,3-b]pyrrole, suspended in 500 ml of ethanol is added to a sodium ethoxide solution freshly prepared by dissolving 24.6 g of sodium in 500 ml of ethanol, and the whole is agitated for 15 minutes; then 125 g of ethyl bromoacetate are added. The whole is refluxed for 4 hours and then hydrolysed by the addition of 600 ml of sodium hydroxide solution (N). The whole is refluxed for 30 minutes and the ethanol is eliminated by distillation. The cooled solution is then filtered. The filtrate is acidified to a pH of approximately 3, and the precipitate obtained is washed with water and recrystallised in a mixture of benzene and cyclohexane. In this manner 150 g of 3-methyl-5-benzoyl-6-carboxymethylthieno[2,3-b]pyrrole are obtained; m.p.=197° C.

Workup

  1. customfreshly prepared
  2. temperatureThe whole is refluxed for 4 hours
  3. temperatureThe whole is refluxed for 30 minutes
  4. distillationthe ethanol is eliminated by distillation
  5. filtrationThe cooled solution is then filtered
  6. customthe precipitate obtained
  7. washis washed with water
  8. customrecrystallised in a mixture of benzene and cyclohexane

Sources & evidence

ORD record
ord-ff871bd757994a09883fcd37761d9ade
Source dataset
uspto-grants-1986_01
Patent number
US04567196

Reaction notes

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