Dimethylformamide → HCID 1226728, compound

HRID 1084824Notes

Reaction equation

HRID 1084824 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14])=[O:9].[C:20](=O)([O-])[O-].[K+].[K+].CN(C)C=O.CI>CC(C)=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([O:15][CH3:20])=[O:14])=[O:9]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 3063368HCID 3063368, compound

Product 1

HCID 1226728HCID 1226728, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 2-[3-(2-thienyl)acrylamido]benzoic acid (273 mg, 1 mmol) in dry acetone (2 ml) were added potassium carbonate (194 mg, 1.4 mmol) and dry dimethylformamide (1 ml). The mixture was treated with methyl iodide (199 mg, 1.4 mmol) and dry dimethylformamide (2 ml) and stirred at room temperature for 3 hours. The reaction mixture was poured into ice water, the precipitated solid was collected on a filter by suction, dried, and recrystallized from the mixed solvent of methanol and water to give pale yellow crystals of the desired compound (213 mg, yield, 74%). m.p., 126°-127° C.

Workup

  1. customthe precipitated solid was collected on
  2. filtrationa filter by suction
  3. customdried
  4. customrecrystallized from the mixed solvent of methanol and water

Sources & evidence

ORD record
ord-bbf74cbe8e1d4834beecf124acec8e88
Source dataset
uspto-grants-1991_04
Patent number
US05006548

Reaction notes

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