Triethylamine → HCID 2970608, compound

HRID 1520338Notes

Reaction equation

HRID 1520338 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8].CCN(CC)CC.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[N:20][CH:19]=1>C1COCC1>[C:7]([C:6]1[CH:5]=[CH:4][S:3][C:2]=1[NH:1][C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[N:20][CH:19]=1)(=[O:8])[NH2:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 82604Nicotinoyl chlorideHCID 6994952-Aminothiophene-3-carboxamide

Product 1

HCID 2970608HCID 2970608, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-aminothiophene-3-carboxamide (800 mg, 5.63 mmol, 1.0 eq.) in THF (15 mL) and Et3N (626 mg, 6.19 mmol, 1.1 eq.) was added nicotinoyl chloride (795 mg, 5.63 mmol, 1.0 eq.) in anhydrous THF (15 mL) dropwise. The resulted mixture was stirred at room temperature overnight. After the reaction was completed, the volatiles were evaporated. The residue was washed with CH2Cl2 (20 mL). The resulting solid was collected and dried in vacuo to give 1.50 g of N-(3-carbamoylthiophen-2-yl)nicotinamide as a brown solid (quantitative yield). LCMS m/z=248.1 (M+1) (Method B) (retention time=1.34 min).

Workup

  1. customthe volatiles were evaporated
  2. washThe residue was washed with CH2Cl2 (20 mL)
  3. customThe resulting solid was collected
  4. customdried in vacuo

Sources & evidence

ORD record
ord-d58f63c7dfc94a4a9828479e3303f9d2
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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