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

HRID 436397Notes

Reaction equation

HRID 436397 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 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 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-fa0fb77e5cd84f369e3c2fe629cc3db2
Source dataset
uspto-grants-1977_02
Patent number
US04009160

Reaction notes

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