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

HRID 2082776Notes

Reaction equation

HRID 2082776 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-7b386d27c6a64d218a969db593bdd9f3
Source dataset
uspto-grants-1978_04
Patent number
US04082771

Reaction notes

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