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

HRID 568126Notes

Reaction equation

HRID 568126 reaction equation
S(=O)(=O)(O)O.Cl.[S:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH2:12][CH2:13][NH:14][CH:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25])[C:16](N)=[O:17].Cl.[CH3:27][OH:28]>>[ClH:25].[S:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH2:12][CH2:13][NH:14][CH:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25])[C:16]([O:28][CH3:27])=[O:17]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1118Sulfuric AcidHCID 21953219[2-(2-Thienyl)ethylamino](2-chlorophenyl)acetamide hydrochloride

Product 1

HCID 24820193Methyl 2-(2-chlorophenyl)-2-((2-(thiophen-2-yl)ethyl)amino)acetate hydrochloride

Procedure

21.5 ml (0.4 mol) of 100% sulfuric acid is dissolved, under cooling in 100 ml of methanol, the solution is heated under reflux for ½ hour, then cooled to room temperature and to it 33.1 g (0.1 mol) of [2-(2-thienyl)ethylarnino](2-chlorophenyl)acetamide hydrochloride, prepared as described in Example 5., is added and the mixture is heated under reflux conditions for 10 hours. Methanol is then distilled off in vacuo and to the residue 150 ml of 1,2-dichloroethane and 150 ml of water are added, shaken well, and the two phases are separated. The aqueous layer is extracted with 2×30 ml of 1,2-dichloroethane, the combined organic layers are washed with 80 ml of 5% sodium hydroxide solution, then with 100 ml of water, dried over anhydrous sodium sulfate and evaporated in vacuo. Weight of the residue: 28.5 g. The oily product, which is the base of formula (VIII), is dissolved in 50 ml of isopropyl acetate, 7.3 ml (0.087 mol) of concentrated hydrochloric acid solution is added to it, and the mixture is stirred at room temperature for 1 hour. The precipitating product is filtered off, washed with 2×10 ml of isopropyl acetate and dried. Weight: 28.4 g (82%) mp.: 177-178° C. (lit. 175° C.).

Workup

  1. temperaturethe solution is heated
  2. temperatureunder reflux for ½ hour
  3. customprepared
  4. addition, is added
  5. temperaturethe mixture is heated under reflux conditions for 10 hours
  6. distillationMethanol is then distilled off in vacuo and to the residue 150 ml of 1,2-dichloroethane and 150 ml of water
  7. additionare added
  8. customthe two phases are separated
  9. extractionThe aqueous layer is extracted with 2×30 ml of 1,2-dichloroethane
  10. washthe combined organic layers are washed with 80 ml of 5% sodium hydroxide solution
  11. dry with materialwith 100 ml of water, dried over anhydrous sodium sulfate
  12. customevaporated in vacuo
  13. dissolutionis dissolved in 50 ml of isopropyl acetate
  14. stirringthe mixture is stirred at room temperature for 1 hour
  15. filtrationThe precipitating product is filtered off
  16. washwashed with 2×10 ml of isopropyl acetate
  17. customdried
  18. custom28.4 g (82%) mp.: 177-178° C. (lit. 175° C.)

Sources & evidence

ORD record
ord-46d2a8a870ef4604ae6c08bee73edc7c
Source dataset
uspto-grants-2001_01
Patent number
US06180793B2

Reaction notes

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