Hydrochloric Acid → 2-[2-(5-Chloro-2-methoxybenzoylamino)ethyl]-5-(methyl-aminothiocarbonylaminosulfonyl)thiophene

HRID 482025Notes

Reaction equation

HRID 482025 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([CH:21]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]1[S:13][C:14]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:15][CH:16]=1)=[O:8].C[N:25]=[C:26]=[S:27].Cl.[CH3:29]N(C=O)C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([CH:21]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]1[S:13][C:14]([S:17]([N:18]([CH3:29])[C:26]([NH2:25])=[S:27])(=[O:19])=[O:20])=[CH:15][CH:16]=1)=[O:8]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 11167Methyl isothiocyanateHCID 152886722-[2-(5-Chloro-2-methoxybenzoylamino)ethyl]-5-sulfamoylthiophene

Product 1

HCID 867530092-[2-(5-Chloro-2-methoxybenzoylamino)ethyl]-5-(methyl-aminothiocarbonylaminosulfonyl)thiophene

Conditions

Temperature
60 °C

Procedure

375 mg of 2-[2-(5-chloro-2-methoxybenzoylamino)ethyl]-5-sulfamoylthiophene were dissolved in 3 ml of absolute DMF together with 415 mg of K2 CO3 and 90 mg of methyl isothiocyanate, and the mixture was then stirred for 3 h at 60° C. The cooled solution was introduced into 2N HCl and the resulting precipitate was filtered off with suction. The dried residue was chromatographed on silica gel using the eluent system ethyl acetate/toluene 1:1.

Workup

  1. filtrationthe resulting precipitate was filtered off with suction
  2. customThe dried residue was chromatographed on silica gel using the eluent system ethyl acetate/toluene 1:1

Sources & evidence

ORD record
ord-357659a0086b4f10a5b8ee590c545277
Source dataset
uspto-grants-1998_08
Patent number
US05792788

Reaction notes

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