Chloroform → HCID 67550799, compound

HRID 1368966Notes

Reaction equation

HRID 1368966 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-50b34b7b7e3046a2885a9fb2d714aa70
Source dataset
uspto-grants-2003_06
Patent number
US06576653B2

Reaction notes

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