Acetyl chloride → HCID 21914132, compound
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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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 stiffing. 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
- customa precipitate formed
- customThe ice bath was removed
- waitto sit for 15 minutes
- additionIce water (250 ml) was added
- filtrationThe sample was filtered
- washrinsed with water and trichloromethane
- waitswirled for 10 minutes
- additionTrichloromethane (200 ml) was added
- stirringthe mixture was stirred
- filtrationfiltered
- washrinsed with water and trichloromethane
- customdried to the air overnight
Sources & evidence
- ORD record
- ord-8b383d40bee2406cb56d575578281032
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247432B2
Reaction notes
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