Sodium Hydroxide → (2-(5-Chloro-2-methoxybenzoylamino)ethyl]-5-(methylaminocarbonylaminosulfonyl)thiophene

HRID 482022Notes

Reaction equation

HRID 482022 reaction equation
[OH-].[Na+].[CH3:3][NH:4][C:5](=[O:10])C(Cl)(Cl)Cl.[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([O:32][CH3:33])=[C:16]([CH:31]=1)[C:17]([NH:19][CH2:20][CH2:21][C:22]1[S:23][C:24]([S:27](=[O:30])(=[O:29])[NH2:28])=[CH:25][CH:26]=1)=[O:18]>CS(C)=O>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([O:32][CH3:33])=[C:16]([CH:31]=1)[C:17]([NH:19][CH2:20][CH2:21][C:22]1[S:23][C:24]([S:27]([NH:28][C:5]([NH:4][CH3:3])=[O:10])(=[O:29])=[O:30])=[CH:25][CH:26]=1)=[O:18]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2486522,2,2-Trichloro-n-methylacetamideHCID 152886722-[2-(5-Chloro-2-methoxybenzoylamino)ethyl]-5-sulfamoylthiophene

Product 1

HCID 9802837(2-(5-Chloro-2-methoxybenzoylamino)ethyl]-5-(methylaminocarbonylaminosulfonyl)thiophene

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

120 mg of powdered NaOH and 141 mg of N-methyltrichloro-acetamide (0.8 mmol) were added to 299 mg (0.8 mmol) of 2-[2-(5-chloro-2-methoxybenzoylamino)ethyl]-5-sulfamoyl-thiophene in 9 ml of DMSO. The mixture was stir 65° C. for 1.5 hours. After cooling, it was stirred into ice water of pH 2. The precipitate was filtered off with suction and taken up in CH2Cl2, and the solution was washed with water and dried using MgSO4. After evaporating the solvent, a yellow-brown crude product remained which, after treatment with CH2Cl2 /5% methanol, crystallized at -4° C.

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitate was filtered off with suction
  3. washthe solution was washed with water
  4. customdried
  5. customAfter evaporating the solvent
  6. customafter treatment with CH2Cl2 /5% methanol, crystallized at -4° C.

Sources & evidence

ORD record
ord-16b3842ff8724a55bc81d390fd245322
Source dataset
uspto-grants-1998_08
Patent number
US05792788

Reaction notes

Loading…