Lithium Hydroxide → 3-(N-methyl-N-(2-morpholinoethyl)-sulfamoyl)thiophene-2-carboxylic acid

HRID 59744Notes

Reaction equation

HRID 59744 reaction equation
[CH3:1][N:2]([CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[S:3]([C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]([O:13]C)=[O:12])(=[O:5])=[O:4].C1COCC1.[OH-].[Li+]>O>[CH3:1][N:2]([CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[S:3]([C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]([OH:13])=[O:12])(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86703847methyl 3-(N-methyl-N-(2-morpholinoethyl)sulfamoyl)thiophene-2-carboxylate

Product 1

HCID 867038483-(N-methyl-N-(2-morpholinoethyl)-sulfamoyl)thiophene-2-carboxylic acidYield 83.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 3-(N-methyl-N-(2-morpholinoethyl)sulfamoyl)-thiophene-2-carboxylate (Int. 47) (510 mg, 1.464 mmol) in a 1:1 mixture of THF and H2O, lithium hydroxide (351 mg, 14.64 mmol) was added, and the mixture was stirred at RT overnight. The organic solvent was evaporated and the aqueous residue was acidified with 2N HCl (pH=7); the precipitate was collected by filtration affording 3-(N-methyl-N-(2-morpholinoethyl)-sulfamoyl)thiophene-2-carboxylic acid (Int. 48) (410 mg, 1.226 mmol, MS/ESI+334.9 [MH]+).

Workup

  1. additionwas added
  2. customThe organic solvent was evaporated
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-7d2ad349bc04497f86566dd48e2360a3
Source dataset
uspto-grants-2016_09
Patent number
US09440954B2

Reaction notes

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