Water → HCID 21196008, compound
Reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:24]=[CH:23][C:10]([O:11][CH2:12][C:13]2[N:14]([CH3:22])[C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:9][CH:8]=1.O.[OH-].[Na+].CN(C)[CH:30]=[O:31]>>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([O:11][CH2:12][C:13]2[N:14]([CH3:22])[C:15]3[C:20]([C:21]=2[CH:30]=[O:31])=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:23][CH:24]=1Participants
Conditions
- Temperature
- 55 °C
Procedure
Under a nitrogen atmosphere a round bottom flask was charged with 0.63 ml of anhydrous N,N-dimethylformamide. The reaction vessel was placed in a −20° C. bath and then phosphorous oxychloride (0.187 ml, 0.310 g, 2.02 mmol) was carefully added. The resulting mixture was stirred in an ice bath for about twenty minutes and 2-[(4-chlorophenoxy)methyl]-1-methyl-1H-indole (0.50 g, 1.84 mmol) in 3.4 ml of N,N-dimethylformamide, was added. The resulting mixture was stirred at room temperature for about ninety minutes. The reaction mixture was then placed over an oil bath and heated to 55° C. and maintained at this temperature for about one hour. The reaction mixture was then permitted to cool to room temperature and was then poured into water. Sodium hydroxide (10 ml of a 5.0 N solution) was added and heated to reflux. The resulting mixture was cooled and the solids were then collected by filtration.
Workup
- customwas placed in a −20° C.
- stirringThe resulting mixture was stirred at room temperature for about ninety minutes
- customThe reaction mixture was then placed over an oil bath
- temperaturemaintained at this temperature for about one hour
- temperatureto cool to room temperature
- temperatureheated to reflux
- temperatureThe resulting mixture was cooled
- filtrationthe solids were then collected by filtration
Sources & evidence
- ORD record
- ord-98725d0115a54e61b46d84bf41f20ab7
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06245761B1
Reaction notes
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