Acetyl chloride → HCID 21914132, compound

HRID 1246190Notes

Reaction equation

HRID 1246190 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]([C:18]([NH2:20])=[O:19])[CH2:12]2.[C:21](Cl)(=[O:23])[CH3:22]>ClC(Cl)Cl>[C:21]([N:14]1[C:15]2[C:11](=[CH:10][C:9]([Cl:8])=[CH:17][CH:16]=2)[CH2:12][CH:13]1[C:18]([NH2:20])=[O:19])(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21914136HCID 21914136, compound

Product 1

HCID 21914132HCID 21914132, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
5 °C

Procedure

Triethylamine (0.02080 mole) was added to intermediate (7) (0.09632 mole) dissolved in trichloromethane (700 ml). The mixture was cooled to 5° C. Acetyl chloride (0.2480 mole) was added over 2 minutes with stirring. After 5 minutes, a precipitate formed. The ice bath was removed, and the container allowed to sit for 15 minutes. Ice water (250 ml) was added, and the mixture was stirred for 10 minutes. The sample was filtered, rinsed with water and trichloromethane. The solid was suspended in water (200 ml), and swirled for 10 minutes. Trichloromethane (200 ml) was added and the mixture was stirred, then filtered and rinsed with water and trichloromethane, and then dried to the air overnight, yielding 19.71 g of 1-acetyl-5-chloro-2,3-dihydro-1H-indole-2-carboxamide (intermediate 8).

Workup

  1. customa precipitate formed
  2. customThe ice bath was removed
  3. waitto sit for 15 minutes
  4. additionIce water (250 ml) was added
  5. stirringthe mixture was stirred for 10 minutes
  6. filtrationThe sample was filtered
  7. washrinsed with water and trichloromethane
  8. waitswirled for 10 minutes
  9. additionTrichloromethane (200 ml) was added
  10. stirringthe mixture was stirred
  11. filtrationfiltered
  12. washrinsed with water and trichloromethane
  13. customdried to the air overnight

Sources & evidence

ORD record
ord-de8aef574919401483f67dc4a3dd343a
Source dataset
uspto-grants-2006_10
Patent number
US07125891B2

Reaction notes

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