Hydrochloric Acid → Methyl 2-(2-chlorophenyl)-2-((2-(thiophen-2-yl)ethyl)amino)acetate hydrochloride

HRID 1384481Notes

Reaction equation

HRID 1384481 reaction equation
S(=O)(=O)(O)O.[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH2:11][CH2:12][NH:13][CH:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:24])[C:15](N)=[O:16].[ClH:25].[CH3:26][OH:27]>>[ClH:24].[CH3:26][O:27][C:15](=[O:16])[CH:14]([NH:13][CH2:12][CH2:11][C:7]1[S:6][CH:10]=[CH:9][CH:8]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:25]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1118Sulfuric AcidHCID 9882604[2-(2-Thienyl)ethylamino](2-chlorophenyl)acetamide

Product 1

HCID 24820193Methyl 2-(2-chlorophenyl)-2-((2-(thiophen-2-yl)ethyl)amino)acetate hydrochlorideYield 83%

Procedure

In 40 ml of methanol under cooling 11.5 ml (0.215 mol) of 100% sulfuric acid is dissolved, the solution is heated under reflux conditions for 30 minutes, then after cooling to room temperature 12.4 g (0.042 mol) of dextrorotatory [2-(2-thienyl)ethylamino](2-chlorophenyl)acetamide is added and the mixture is heated under reflux for 6-7 hours, till the end of the reaction. Methanol is distilled off in vacuo, to the residue 75 ml of 1,2-dichloroethane and 75 ml of water are added, the mixture is shaken well and the phases are separated. The aqueous phase is extracted with 2×20 ml of 1,2-dichloroethane, the united organic phase is extracted with 50 ml of 5% sodium hydroxide solution then with 50 ml of water, dried over anhydrous sodium sulfate. The drying material is filtered off and 1.5 g (0.041 mol of dry hydrogen chloride gas is introduced under cooling into the solution. The precipitated crystalline product is filtered off, washed with 1,2-dichloroethane and dried. Weight: 12.1 g, mp.: 185-186° C. (decomposition), [α]22D=+107° . Yield: 83%. Optical purity: in general 99-100%.

Workup

  1. dissolutionis dissolved
  2. temperaturethe solution is heated under reflux conditions for 30 minutes
  3. additionis added
  4. temperaturethe mixture is heated
  5. temperatureunder reflux for 6-7 hours, till the end of the reaction
  6. distillationMethanol is distilled off in vacuo, to the residue 75 ml of 1,2-dichloroethane and 75 ml of water
  7. additionare added
  8. customthe phases are separated
  9. extractionThe aqueous phase is extracted with 2×20 ml of 1,2-dichloroethane
  10. extractionthe united organic phase is extracted with 50 ml of 5% sodium hydroxide solution
  11. dry with materialwith 50 ml of water, dried over anhydrous sodium sulfate
  12. filtrationThe drying material is filtered off
  13. temperatureunder cooling into the solution
  14. filtrationThe precipitated crystalline product is filtered off
  15. washwashed with 1,2-dichloroethane
  16. customdried

Sources & evidence

ORD record
ord-0475d3c999114f0884ff81d82b986ed3
Source dataset
uspto-grants-2001_07
Patent number
US06258961B1

Reaction notes

Loading…