Potassium Carbonate → methyl 3-(N-methyl-N-(2-morpholinoethyl)sulfamoyl)thiophene-2-carboxylate

HRID 59743Notes

Reaction equation

HRID 59743 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]([O:13][CH3:14])=[O:12])(=[O:5])=[O:4].C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>CN(C=O)C>[CH3:1][N:2]([CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)[S:3]([C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]([O:13][CH3:14])=[O:12])(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 12906749methyl 3-(N-methylsulfamoyl)thiophene-2-carboxylate

Product 1

HCID 86703847methyl 3-(N-methyl-N-(2-morpholinoethyl)sulfamoyl)thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-(N-methylsulfamoyl)thiophene-2-carboxylate (prepared in an analogous manner as described in Example 10, Scheme 10, Step 1, 530 mg, 2.253 mmol) in dry DMF (20 ml) under nitrogen atmosphere, K2CO3 (623 mg, 4.51 mmol) and 4-(2-chloroethyl)morpholine hydrochloride (838 mg, 4.51 mmol) were added, and the mixture was reacted at 60° C. overnight and then at 80° C. for 5 hours. The insoluble inorganic salts were filtered off, the filtrate was evaporated and the residue was purified by flash chromatography on silica gel (DCM/MeOH=9/1) to afford methyl 3-(N-methyl-N-(2-morpholinoethyl)sulfamoyl)thiophene-2-carboxylate (Int. 47) (510 mg, 1.464 mmol, MS/ESI+348.8 [MH]+).

Workup

  1. customthe mixture was reacted at 60° C. overnight
  2. filtrationThe insoluble inorganic salts were filtered off
  3. customthe filtrate was evaporated
  4. customthe residue was purified by flash chromatography on silica gel (DCM/MeOH=9/1)

Sources & evidence

ORD record
ord-3b503707a4cf4c79bc3e262e1dc90723
Source dataset
uspto-grants-2016_09
Patent number
US09440954B2

Reaction notes

Loading…