Chloroform → HCID 67550799, compound

HRID 2184685Notes

Reaction equation

HRID 2184685 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].[CH:14]([Cl:17])(Cl)Cl.[Cl:18]N1C(=O)CCC1=O>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>[CH2:1]([O:3][C:4]([C:6]1[NH:10][C:9]2[S:11][C:12]([Cl:18])=[CH:13][C:8]=2[C:14]=1[Cl:17])=[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 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterSolvent

Procedure

To a 0° C. solution of 6H-thieno[2,3-b]pyrrole-5carboxylic acid ethyl ester (180 mg, 0.92 mmol) in acetic add (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-70cd8937d80e4cf2b810523e177930a1
Source dataset
uspto-grants-2002_06
Patent number
US06399601B1

Reaction notes

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