Water → HCID 10934323, compound

HRID 2122103Notes

Reaction equation

HRID 2122103 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Cl[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=1[N+:18]([O-:20])=[O:19].[N+:21]([CH2:24][CH3:25])([O-:23])=[O:22].O>C1(C)C=CC=CC=1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[N+:18]([C:9]1[CH:10]=[C:11]([C:14]([F:17])([F:16])[F:15])[CH:12]=[CH:13][C:8]=1[CH:24]([N+:21]([O-:23])=[O:22])[CH3:25])([O-:20])=[O:19]

Participants

7

Reactant 4

HCID 962WaterHCID 6587NitroethaneHCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 10340Sodium Carbonate

Product 1

HCID 10934323HCID 10934323, compoundYield 13.6%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

0.87 g of sodium carbonate in 5 ml of anhydrous toluene are placed in a 30 ml reaction vessel, and 0.11 g of benzyltriethylammonium chloride and 1.13 g of 4-chloro-3-nitrobenzotrifluoride and 0.38 g of nitroethane are added at the same time. The mixture is stirred for 16 hours at 20° C., 10 ml of water are added and the aqueous phase is separated, then acidified by a 4N solution of sulfuric acid. It is then extracted with 5 ml of methyl t-butyl ether. After removing the organic solvent, 0.18 g of a mixture is obtained which is separated by column chromatography using reverse phase silica eluting with a mixture of water and acetonitrile to obtain 0.12 g of the title compound, m.p. 48° C.

Workup

  1. additionare added at the same time
  2. customthe aqueous phase is separated
  3. extractionIt is then extracted with 5 ml of methyl t-butyl ether
  4. customAfter removing the organic solvent

Sources & evidence

ORD record
ord-a41c903ad24742d68c436ba338a87aab
Source dataset
uspto-grants-2004_02
Patent number
US06696613B2

Reaction notes

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