Hydrochloric Acid → HCID 86639600, compound

HRID 1674595Notes

Reaction equation

HRID 1674595 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([N:24]([CH3:26])C)=[C:17]([C:20]([F:23])([F:22])[F:21])[CH:18]=3)[CH:13]=[CH:12]2)=[CH:7][CH:6]=1)[CH3:2].P(Cl)(Cl)(Cl)=O.[OH-].[Na+].Cl.CN(C)[CH:38]=[O:39]>>[CH2:1]([O:3][C:4](=[O:27])[C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([NH:24][CH3:26])=[C:17]([C:20]([F:22])([F:23])[F:21])[CH:18]=3)[C:13]([CH:38]=[O:39])=[CH:12]2)=[CH:9][CH:10]=1)[CH3:2]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 58437447HCID 58437447, compound

Product 1

HCID 86639600HCID 86639600, compound

Procedure

To a solution of 4-(5-dimethylamino-6-trifluoromethylindol-1-yl)benzoic acid ethyl ester (0.054 g) in N,N-dimethylformamide (2 mL) was added phosphoryl chloride (0.026 g) under ice cooling, and this mixture was stirred at room temperature for 16 hours. To this mixture was added 2 mol/L aqueous sodium hydroxide solution (5 mL), and this resulting mixture was stirred at 50° C. for 30 minutes. After cooling to ambient temperature, 1 mol/L hydrochloric acid (10 mL) was added to this mixture, and the precipitated solid was collected by filtration. This solid was washed with water and n-hexane, dried under reduced pressure at 50° C. to give the title compound (0.026 g).

Workup

  1. stirringthis resulting mixture was stirred at 50° C. for 30 minutes
  2. temperatureAfter cooling to ambient temperature
  3. filtrationthe precipitated solid was collected by filtration
  4. washThis solid was washed with water and n-hexane
  5. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-1cc588b60e1c47648d7bdaf5d4aff146
Source dataset
uspto-grants-2011_08
Patent number
US08003647B2

Reaction notes

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