4-Chlorobenzoyl chloride → HCID 59648618, compound

HRID 1363262Notes

Reaction equation

HRID 1363262 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[S:5]1[C:9]2[NH:10][C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:12][C:8]=2[CH:7]=[CH:6]1.[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1>ClC(Cl)C>[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([C:6]2[S:5][C:9]3[NH:10][C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:12][C:8]=3[CH:7]=2)=[O:24])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 11708220ethyl 6H-thieno[2,3-b]pyrrole-5-carboxylate

Product 1

HCID 59648618HCID 59648618, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Under a N2 atmosphere and at 0° C., to a 40-mL scintillation vial fitted with a magnetic stir bar was added solid aluminum chloride (0.7 g 5.28 mmol) and a solution of ethyl 6H-thieno[2,3-b]pyrrole-5-carboxylate (0.61 g, 3.14 mmol, 0.9 equiv) in solution in 10 mL dichloroethane (DCE). 4-Chlorobenzoyl chloride (0.92 g, 5.28 mmol) was then added at 0° C. and stirring was continued for 2 h as the reaction was allowed to warm to rt. The reaction was cooled and was added to an ice-filled beaker. The aqueous mixture was extracted ×3 with EtOAc. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The resulting residue was purified via ISCO Companion (0-30% gradient EtOAc/heptane over 30 min) to give ethyl 2-(4-chlorobenzoyl)-6H-thieno[2,3-b]pyrrole-5-carboxylate (0.34 g). 1H NMR (400 MHz, CDCl3) δ ppm 1.42 (t, J=7.13 Hz, 3H) 4.43 (q, J=7.13 Hz, 2H) 7.17 (d, J=1.81 Hz, 1H) 7.50 (d, J=8.44 Hz, 2H) 7.59 (s, 1H) 7.77-7.86 (m, 2H) 10.03 (s, 1H).

Workup

  1. customUnder a N2 atmosphere and at 0° C., to a 40-mL scintillation vial fitted with a magnetic stir bar
  2. temperatureThe reaction was cooled
  3. additionfilled beaker
  4. extractionThe aqueous mixture was extracted ×3 with EtOAc
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe resulting residue was purified via ISCO Companion (0-30% gradient EtOAc/heptane over 30 min)

Sources & evidence

ORD record
ord-9b5665527ccf4631bf9caf3a7ed9d3dd
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

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