Potassium Carbonate → HCID 20553510, compound

HRID 1446889Notes

Reaction equation

HRID 1446889 reaction equation
[CH3:1][N:2]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[C:3]1[S:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][N:7]=1.Br[CH:19]([CH3:24])[C:20]([O:22][CH3:23])=[O:21].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH3:1][N:2]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:19]([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:13][CH:12]=1)[C:3]1[S:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 20553512HCID 20553512, compound

Product 1

HCID 20553510HCID 20553510, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-[N-methyl-N-(5-nitro-2-thiazolyl)amino]phenol (2.51 g), methyl 2-bromopropionate (1.67 g), anhydrous potassium carbonate (1.52 g) and methyl ethyl ketone (50 ml) was heated under reflux for a period of 18 hours. The mixture was cooled, extracted with dichloromethane and the organic extract was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to give a brown oil. The crude product was purified by chromatography over silica gel with dichloromethane elution to give the required product (1.2 g) as a colourless oil. The pmr spectrum of the product was consistent with the assigned structure (CDCl3 ; chemical shift δ ppm): 1.65, d, 3H; 3.55, s, 3H; 3.85, s, 3H; 4.80, q, 1H; 7.20, m, 4H; 8.20, s, 1H.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for a period of 18 hours
  3. temperatureThe mixture was cooled
  4. extractionextracted with dichloromethane
  5. extractionthe organic extract
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customto give a brown oil
  9. customThe crude product was purified by chromatography over silica gel with dichloromethane elution

Sources & evidence

ORD record
ord-5de36366e2e4403eaea5ec41cedb0f54
Source dataset
uspto-grants-1982_02
Patent number
US04314065

Reaction notes

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