Diethyl Ether → HCID 13070047, compound

HRID 1759594Notes

Reaction equation

HRID 1759594 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[OH-].[Na+].[CH2:17]([SH:19])[CH3:18].CCOCC>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl.O>[N+:12]([C:5]1[CH:4]=[CH:3][C:2]([S:19][CH2:17][CH3:18])=[CH:7][C:6]=1[C:8]([F:11])([F:10])[F:9])([O-:14])=[O:13]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 6343EthanethiolHCID 14798Sodium HydroxideHCID 670525-Chloro-2-nitrobenzotrifluoride2×

Product 1

HCID 13070047HCID 13070047, compound

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-chloro-2-nitrobenzotrifluoride (150 g., 0.67 mole) and benzyltriethylammonium chloride (15 g., 0.067 mole) phase transfer catalyst in methylene chloride (1500 ml) is added to a cold (0°-5° C.) stirred solution of sodium hydroxide (53.2 g., 1.33 moles) and ethanethiol (97.47 g., 1.57 moles) in water (1200 ml) over a 1.5-2 hour period. The reaction mixture is allowed to come to room temperature and is stirred for 17 hours. Thin layer chromatography on silica gel with 10 percent ether-90 percent petroleum ether (b.p. 30°-60° C.) diluent indicates all of the 5-chloro-2-nitrobenzotrifluoride has reacted. The methylene chloride layer is then separated from the aqueous layer and washed with water. The methylene chloride is removed by evaporation leaving 2-nitro-5-ethylthiobenzotrifluoride as an oil.

Workup

  1. customto come to room temperature
  2. customhas reacted
  3. customThe methylene chloride layer is then separated from the aqueous layer
  4. washwashed with water
  5. customThe methylene chloride is removed by evaporation

Sources & evidence

ORD record
ord-733f59ea13f94f578401128b8f50145a
Source dataset
uspto-grants-1982_07
Patent number
US04341901

Reaction notes

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