Water → HCID 15767436, compound

HRID 1449444Notes

Reaction equation

HRID 1449444 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)([O-:3])=[O:2].[OH-].[K+].[Cl:15][C:16]1[CH:17]=[C:18]([C:24]([F:27])([F:26])[F:25])[CH:19]=[C:20]([Cl:23])[C:21]=1F.O>CS(C)=O.C(Cl)Cl>[Cl:15][C:16]1[CH:17]=[C:18]([C:24]([F:25])([F:26])[F:27])[CH:19]=[C:20]([Cl:23])[C:21]=1[N:8]1[C:9]2[C:5](=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7]1

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 1457664-Nitro-1H-indoleHCID 157026Benzene, 1,3-dichloro-2-fluoro-5-(trifluoromethyl)-

Product 1

HCID 15767436HCID 15767436, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-nitroindole (0.5 g, 3.0 mmol), potassium hydroxide pellets (0.7 g, 12.0 mmol) in 40.0 ml dimethylsulfoxide were stirred for 30 minutes at room temperature. Then 3,5-dichloro-4-fluorobenzotrifluoride was added and stirred at room temperature for 3 hours. Water and methylene chloride were added and the mixture was stirred for 10 minutes. The organic phase was separated, washed with water, dried and stripped under vacuum to yield 1.0 g of yellow solid of the desired product. The structure was confirmed by infrared spectroscopy, mass spectrometry and nuclear magnetic resonance spectroscopy.

Workup

  1. stirringstirred at room temperature for 3 hours
  2. stirringthe mixture was stirred for 10 minutes
  3. customThe organic phase was separated
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-58b324d4d2114364a824ab06c5026b53
Source dataset
uspto-grants-1997_02
Patent number
US05599774

Reaction notes

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