Pyridine → 2-Acetylamino-4-methylthiophene-3-carboxylic acid amide

HRID 1049862Notes

Reaction equation

HRID 1049862 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH3:10])[C:6]=1[C:7]([NH2:9])=[O:8].N1C=CC=CC=1.[C:17](Cl)(=[O:19])[CH3:18]>C(Cl)Cl>[C:17]([NH:1][C:2]1[S:3][CH:4]=[C:5]([CH3:10])[C:6]=1[C:7]([NH2:9])=[O:8])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 2938102-Amino-4-methylthiophene-3-carboxamide

Product 1

HCID 28077082-Acetylamino-4-methylthiophene-3-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-amino-4-methyl-thiophene-3-carboxylic acid amide (5 g, 32 mmol) in DCM (100 mL) is cooled to 0° C. Dry pyridine (3.6 mL, 45 mmol) is added, followed by acetylchloride (11 mL, 156 mmol) which is added dropwise to the solution. The resulting mixture is stirred at room temperature overnight, then diluted with DCM and washed with aqueous NaHCO3. The organic phase is dried over MgSO4, filtered and concentrated. The obtained residue is triturated in di-isopropylether, filtered, and the cake is dried to afford the desired product.

Workup

  1. additionis added dropwise to the solution
  2. washwashed with aqueous NaHCO3
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe obtained residue is triturated in di-isopropylether
  7. filtrationfiltered
  8. customthe cake is dried

Sources & evidence

ORD record
ord-f020cdb56b744c4683dde4f8fed3e3a4
Source dataset
uspto-grants-2016_07
Patent number
US09382254B2

Reaction notes

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