1,2-Dichloroethane → 2-[(1-Benzothien-2-ylcarbonyl)amino]nicotinamide

HRID 1992311Notes

Reaction equation

HRID 1992311 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1[N:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15](O)=[O:16])=[O:11].C(Cl)CCl.[NH3:26]>CN(C1C=CN=CC=1)C.ClCCl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1[N:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([NH2:26])=[O:16])=[O:11]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 591303622-[(1-Benzothien-2-ylcarbonyl)amino]nicotinic acid

Product 1

HCID 591303732-[(1-Benzothien-2-ylcarbonyl)amino]nicotinamideYield 77%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-[(1-benzothien-2-ylcarbonyl)amino]nicotinic acid (112 g, 4.0 mmol), EDC (2.3 g, 12.0 mmol) and DMAP (1.46 g, 12.0 mmol) in anhyd dichloromethane (50 mL) was stirred at room temperature for 2 h. To this mixture was added 40% aqueous ammonia (4.0 mL), and the resulting solution stirred at room temperature overnight. The solvent was removed in vacuo and the resulting solid was washed with satd NH4Cl solution, NaHCO3 solution, and water. The solid was dried to give product as white powder (0.92 g, 77%). HPLC/MS: (M+H)+298.15 m/z Retention time (LC-MS)=2.44 min. 1H NMR (DMSO-D6): 12.25 (1H, s); 8.54(1H, m); 8.21(1H, s); 8.18(1H, d); 8.07(2H, m); 7.52(2H, m); 7.32(1H, m).

Workup

  1. stirringthe resulting solution stirred at room temperature overnight
  2. customThe solvent was removed in vacuo
  3. washthe resulting solid was washed with satd NH4Cl solution, NaHCO3 solution, and water
  4. customThe solid was dried

Sources & evidence

ORD record
ord-91d22d478b5f48eca7b3852d9dd4d1eb
Source dataset
uspto-grants-2010_01
Patent number
US07648986B2

Reaction notes

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