Sodium Hydroxide → 4-(3,4-Dichlorobenzyl)thieno[3,2-b]pyrrole-5-carboxylic acid

HRID 1017735Notes

Reaction equation

HRID 1017735 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:7][N:8]1[C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][C:10]2[S:18][CH:19]=[CH:20][C:9]1=2>C1COCC1.CO>[Cl:3][C:4]1[CH:5]=[C:6]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:7][N:8]1[C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]2[S:18][CH:19]=[CH:20][C:9]1=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 9798664Ethyl 4-(3,4-dichlorobenzyl)thieno[3,2-b]pyrrole-5-carboxylate

Product 1

HCID 6677224-(3,4-Dichlorobenzyl)thieno[3,2-b]pyrrole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (3N, 1.3 ml) was added to a stirred solution of ethyl 4-(3,4-dichlorobenzyl)thieno[3,2-b]pyrrole-5-carboxylate (0.137 g) in THF (2.5 ml) and methanol (2.5 ml). Stirring was continued for 16 hours at ambient temperature, concentrated in vacuo and the residue dissolved in water. Dropwise addition of acetic acid led to precipitation of the product as a white solid which was filtered and dried (0.107 g, 85%), NMR d(DMSO) 5.79 (2H, s), 7.05 (1H, m), 7.28 (2H, m), 7.42 (1H, s), 7.60 (2H, m); M/z (−) 326 (M+), 324, 282, 280.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionthe residue dissolved in water
  3. additionDropwise addition of acetic acid
  4. customled to precipitation of the product as a white solid which
  5. filtrationwas filtered
  6. customdried (0.107 g, 85%), NMR d(DMSO) 5.79 (2H, s), 7.05 (1H, m), 7.28 (2H, m), 7.42 (1H, s), 7.60 (2H, m)

Sources & evidence

ORD record
ord-8e5d9ebb695d44aaaeb819ade8801dc2
Source dataset
uspto-grants-2002_11
Patent number
US06479527B1

Reaction notes

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