Hydrochloric Acid → 2-Methyl-N-(5-methylthiophen-2-yl)propanamide

HRID 27668Notes

Reaction equation

HRID 27668 reaction equation
C([C:5]1[CH:9]=[C:8]([CH3:10])[S:7][C:6]=1[NH:11][C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])(OC)=O.O.O.[I-].[Li+].CCOCC.Cl>N1C(C)=CC(C)=CC=1C>[CH3:10][C:8]1[S:7][C:6]([NH:11][C:12](=[O:16])[CH:13]([CH3:14])[CH3:15])=[CH:5][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 23341602N-(3-Carbomethoxy-5-methyl-2-thienyl)-2-methylpropanamideHCID 23688289Lithium iodide (LiI), dihydrate

Product 1

HCID 233416282-Methyl-N-(5-methylthiophen-2-yl)propanamideYield 86.7%

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent2×

Procedure

N-(3-Carbomethoxy-5-methyl-2-thienyl)-2-methylpropanamide (4.1 g, 0.017 mol), prepared by the method of Example 48, was dissolved in hot collidine (10 ml) and added to a mixture of lithium iodide dihydrate (10.1 g, 0.06 mol) in collidine (20 ml) kept under nitrogen. The reaction mixture was stirred under reflux for 48 hours, cooled and equilibrated between ether (3×50 ml) and 5 N-hydrochloric acid (50 ml). The ethereal solution was washed with water (25 ml), dried (Na2SO4) and evaporated to yield the required product as an off-white solid (2.7 g, 47%) m.p. 96°-97° C. The product was identical to the product described in Example 38.

Workup

  1. temperatureunder reflux for 48 hours
  2. temperaturecooled
  3. washThe ethereal solution was washed with water (25 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-20f01006fd414d4dab39ec0fa82bcd2b
Source dataset
uspto-grants-1980_09
Patent number
US04222946

Reaction notes

Loading…