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

HRID 1448712Notes

Reaction equation

HRID 1448712 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 5N-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-afad9c58544d494699d4c6e89ba2733c
Source dataset
uspto-grants-1980_02
Patent number
US04187232

Reaction notes

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