Ammonium Chloride → HCID 59648482, compound

HRID 1363275Notes

Reaction equation

HRID 1363275 reaction equation
Br[C:2]1[C:9]2[CH:8]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[NH:6][C:5]=2[S:4][CH:3]=1.[NH4+].[Cl-:16]>CN(C=O)C.Cl[Cu]>[Cl:16][C:2]1[C:9]2[CH:8]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[NH:6][C:5]=2[S:4][CH:3]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 59648519HCID 59648519, compound

Product 1

HCID 59648482HCID 59648482, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 3-bromo-6H-thieno[2,3-b]pyrrole-5-carboxylate (0.25 g, 0.93 mmol) in DMF (37.5 mL) was added CuCl (178 mg, 1.85 mmol). The combined reactants were heated to reflux for 7 h, at which time the cooled mixture was diluted with a saturated solution of NH4Cl (20 mL) and extracted with Et2O (3×40 mL). The combined organic fractions were dried over Na2SO4, filtered and the solvent was removed in vacuo. Purification of the crude oil by flash column chromatography (25% EtOAc in hexanes) afforded ethyl 3-chloro-6H-thieno[2,3-b]pyrrole-5-carboxylate (0.18 g, 86% yield).

Workup

  1. temperatureThe combined reactants were heated
  2. temperatureto reflux for 7 h, at which time the cooled mixture
  3. extractionextracted with Et2O (3×40 mL)
  4. dry with materialThe combined organic fractions were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customPurification of the crude oil by flash column chromatography (25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c7c93c45f7a6443e885115c27f55c220
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

Loading…