Potassium Carbonate → N-(3-(thiophen-2-ylthio)propyl)acetamide

HRID 1484931Notes

Reaction equation

HRID 1484931 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[SH:6].Br[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:14])[CH3:13].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5226742-ThiophenethiolHCID 11830025N-(3-bromopropyl)acetamide

Product 1

HCID 58169495N-(3-(thiophen-2-ylthio)propyl)acetamideYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of thiophene-2-thiol (1.8 g, 15.9 mmol, 1.0 eq), N-(3-bromopropyl) acetamide (4.3 g, 23.9 mmol, 1.5 eq) and K2CO3 (4.4 g, 31.8 mmol, 2.0 eq) in CH2Cl2 (50 mL) was stirred at 23° C. for 1 hour. Then the mixture was extracted with CH2Cl2. (3×). The combined organic layers were dried (Na2SO4), filtered and concentrated to give white solid N-(3-(thiophen-2-ylthio)propyl)acetamide (2.5 g, 72.8%); LC-MS (m/z)=215.9 [M+H]+.

Workup

  1. extractionThen the mixture was extracted with CH2Cl2
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-09bae726d9854a82b8c84c65594cb763
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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