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

HRID 1658688Notes

Reaction equation

HRID 1658688 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-4f16571c95f1464fb7ae662e76a40b83
Source dataset
uspto-grants-1976_06
Patent number
US03966710

Reaction notes

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