Trichloroacetyl chloride → HCID 21914138, compound

HRID 1246191Notes

Reaction equation

HRID 1246191 reaction equation
C(N(CC)CC)C.[C:8]([N:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[CH2:13][CH:12]1[C:21]([NH2:23])=O)(=[O:10])[CH3:9].ClC(Cl)(Cl)C(Cl)=O>ClCCl>[C:8]([N:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[CH2:13][CH:12]1[C:21]#[N:23])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chloride2×HCID 8471Triethylamine2×HCID 21914132HCID 21914132, compound

Product 1

HCID 21914138HCID 21914138, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (0.41291 mole) was added to intermediate (8) (0.08258 mole) suspended in dichloromethane (500 ml) at 0° C. Trichloroacetyl chloride (0.20645 mole) was added over 10 minutes. When the reaction appeared sluggish, an additional portion of triethylamine (20 ml) and then more trichloroacetyl chloride (7.6 ml) were added, and the mixture was stirred for 2 hours at low temperature. The ice bath was removed, and the mixture was allowed to sit for 2 hours. This resulted in a darker colored reaction, which was re-cooled to 0° C. Ice cold water (150 ml) was slowly added, and the mixture was stirred for 5 minutes. The layers were separated, and the organic phase was washed (ice cold 3N HCl, saturated NaHCO3), dried, filtered, and concentrated. The residue was triturated in ice cold diethylether (40 ml). Filtration, rinsing with ice cold diethylether (10 ml), yielding 15.13 g of 1-acetyl-5-chloro-2,3-dihydro-1H-indole-2-carbonitrile (intermediate 9, mp. 140–142° C.).

Workup

  1. customThe ice bath was removed
  2. waitto sit for 2 hours
  3. customThis resulted in a darker colored reaction, which
  4. stirringthe mixture was stirred for 5 minutes
  5. customThe layers were separated
  6. washthe organic phase was washed (ice cold 3N HCl, saturated NaHCO3)
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was triturated in ice cold diethylether (40 ml)
  11. filtrationFiltration
  12. washrinsing with ice cold diethylether (10 ml)

Sources & evidence

ORD record
ord-cab645edf2be46a9ab006a72fd72dc6d
Source dataset
uspto-grants-2006_10
Patent number
US07125891B2

Reaction notes

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