Ethyl Bromide → HCID 54303576, compound

HRID 1612646Notes

Reaction equation

HRID 1612646 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].Cl[C:8]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:14]([N+:20]([O-:22])=[O:21])=[CH:13][C:9]=1[C:10](O)=O.[CH2:23]([SH:25])[CH3:24].[CH2:26](Br)C>CN(C)C=O>[CH2:1]([O:4][C:23](=[S:25])[C:24]1[CH:13]=[C:14]([N+:20]([O-:22])=[O:21])[CH:15]=[C:16]([N+:17]([O-:19])=[O:18])[C:8]=1[CH2:9][CH3:10])[CH3:26]

Participants

6

Reactant 4

HCID 6332Ethyl BromideHCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 172472-Chloro-3,5-dinitrobenzoic acid

Product 1

HCID 54303576HCID 54303576, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent4×

Conditions

Temperature
-5 °C

Procedure

33.2 g (0.240 mol) of potassium carbonate are introduced into 100 ml of dimethylformamide and cooled to -5° C. 37.5 g (0.114 mol) of 2-chloro-3,5-dinitrobenzoic acid (75% with 25% water) dissolved in 120 ml of dimethylformamide are then added over a period of 20 minutes during which time the internal temperature is maintained at from -5° to 0° C. 8.9 ml (0.12 mol) of ethyl mercaptan in 20 ml of dimethylformamide are then added dropwise at -8° C. over a period of 20 minutes. The batch is then stirred for one hour at that same temperature and afterwards the temperature is raised to room temperature over a period of 19 hours. 9.0 ml (0.12 mol) of ethyl bromide in 20 ml of dimethylformamide are then added dropwise over a period of 10 minutes and the reaction mixture is subsequently stirred for 24 hours at room temperature and then poured onto 500 ml of ice/water, stirred and filtered. The material obtained by filtering with suction is washed with water and then dried at room temperature in vacuo and in the presence of phosphorus pentoxide.

Workup

  1. additionare then added over a period of 20 minutes during which time the internal temperature
  2. temperatureis maintained at from -5° to 0° C
  3. temperatureafterwards the temperature is raised to room temperature over a period of 19 hours
  4. stirringthe reaction mixture is subsequently stirred for 24 hours at room temperature
  5. stirringstirred
  6. filtrationfiltered
  7. customThe material obtained
  8. filtrationby filtering with suction
  9. washis washed with water
  10. dry with materialdried at room temperature in vacuo and in the presence of phosphorus pentoxide

Sources & evidence

ORD record
ord-e50ccd7b0d294838b12d34e604a99fc8
Source dataset
uspto-grants-1993_03
Patent number
US05190928

Reaction notes

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