Chloroform → HCID 67550799, compound

HRID 2306796Notes

Reaction equation

HRID 2306796 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:10][C:9]2[S:11][CH:12]=[CH:13][C:8]=2C=1)=[O:5])[CH3:2].[Cl:14]N1C(=O)CCC1=O.[CH:22]([Cl:25])(Cl)Cl>C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[NH:10][C:9]2[S:11][C:12]([Cl:14])=[CH:13][C:8]=2[C:22]=1[Cl:25])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 31398ChlorosuccinimideHCID 11708220ethyl 6H-thieno[2,3-b]pyrrole-5-carboxylate

Product 1

HCID 67550799HCID 67550799, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a 0° C. solution of 6H-thieno[2,3-b]pyrrole-5-carboxylic acid ethyl ester (180 mg, 0.92 mmol) in acetic acid (2 mL) and CHCl3 (2 mL) was added N-chlorosuccinimide (294 mg, 2.2 mmol) over 30 min. The reaction mixture was slowly allowed to warm to room temperature over several hours, stirred overnight, concentrated to remove the chloroform, diluted with water, basified with 5 N NaOH, and extracted with ethyl acetate. The combined organic phases were washed with saturated aqueous NaHCO3, dried over MgSO4, and concentrated. The product was purified by Chromatron-chromatography (4:1 hexanes:ether) and obtained as a white solid (180 mg, 74%).

Workup

  1. concentrationconcentrated
  2. customto remove the chloroform
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic phases were washed with saturated aqueous NaHCO3
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe product was purified by Chromatron-chromatography (4:1 hexanes:ether)

Sources & evidence

ORD record
ord-4c6fb1b5bf494a399ba47579a504cb46
Source dataset
uspto-grants-2004_12
Patent number
US06828343B2

Reaction notes

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