Hydrochloric Acid → HCID 70979966, compound

HRID 1403216Notes

Reaction equation

HRID 1403216 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:15])=[C:6]([C:8]2[NH:9][CH:10]=[CH:11][C:12]=2[C:13]#[N:14])[CH:7]=1.[C:16](Cl)(=[O:18])[CH3:17].[Cl-].[Cl-].[Cl-].[Al+3].Cl>C(Cl)Cl>[C:16]([C:10]1[NH:9][C:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[CH3:15])=[C:12]([C:13]#[N:14])[CH:11]=1)(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 70979614HCID 70979614, compound

Product 1

HCID 70979966HCID 70979966, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-(5-chloro-2-methyl-phenyl)-1H-pyrrole-3-carbonitrile (1.80 g, 8.28 mmol) in DCM (40 mL) was added acetyl chloride (0.936 mL, 13.14 mmol) at room temperature, under nitrogen. The resultant mixture was cooled to 0° C. and anhydrous aluminum trichloride (2.62 g, 19.8 mmol) was added in small portions during a period of 10 min, keeping the internal temperature below 5° C. Upon complete addition, the mixture was brought to room temperature and allowed to stir for 30 min. Then, the mixture was slowly poured in a solution of ice-cooled 1 M HCl (18 mL). The aqueous layer was separated and extracted twice with DCM (40 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The crude material was chromatographed on silica gel (10 to 20% EtOAc/hexane) to afford the title compound (2.0 g, 86%).

Workup

  1. customthe internal temperature below 5° C
  2. additionUpon complete addition
  3. customwas brought to room temperature
  4. additionThen, the mixture was slowly poured in a solution of ice-
  5. customThe aqueous layer was separated
  6. extractionextracted twice with DCM (40 mL)
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customThe crude material was chromatographed on silica gel (10 to 20% EtOAc/hexane)

Sources & evidence

ORD record
ord-9fb9b051871640d09b2bf7b093e060a5
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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