Acetic Anhydride → N-[(3-Methylthiophen-2-yl)methyl]acetamide

HRID 1973343Notes

Reaction equation

HRID 1973343 reaction equation
[NH2:1][CH2:2][C:3]1[S:4][CH:5]=[CH:6][C:7]=1[CH3:8].[C:9](OC(=O)C)(=[O:11])[CH3:10]>N1C=CC=CC=1>[C:9]([NH:1][CH2:2][C:3]1[S:4][CH:5]=[CH:6][C:7]=1[CH3:8])(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 2798756(3-Methylthiophen-2-yl)methanamine

Product 1

HCID 21452353N-[(3-Methylthiophen-2-yl)methyl]acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Aminomethyl-3-methylthiophene (H. D. Hartough, et al., J. Am. Chem. Soc., 70, 4018 [1948]) is dissolved in pyridine and treated with excess acetic anhydride overnight. The solvent is removed under reduced pressure, the residue dissolved in ethyl acetate and washed with dilute hydrochloric acid and sodium bicarbonate solution. The organic extract is dried over magnesium sulfate and evaporated to yield the desired compound.

Workup

  1. customThe solvent is removed under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with dilute hydrochloric acid and sodium bicarbonate solution
  4. extractionThe organic extract
  5. dry with materialis dried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-301357210b024dad95e32fbcda134287
Source dataset
uspto-grants-1976_12
Patent number
US03997527

Reaction notes

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