Dimethylamine → N,N-dimethyl-4-sulfamoylbenzamide

HRID 1914709Notes

Reaction equation

HRID 1914709 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(O)=[O:2].[C:14](N1C=CN=C1)([N:16]1C=CN=[CH:17]1)=O.CNC>C1COCC1>[NH2:13][S:10]([C:7]1[CH:8]=[CH:9][C:4]([C:1]([N:16]([CH3:17])[CH3:14])=[O:2])=[CH:5][CH:6]=1)(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8739CarzenideHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 10353728N,N-dimethyl-4-sulfamoylbenzamideYield 72.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-carboxybenzenesulfonamide (5 g; 24.8 mmol; 1 eq) in THF (75 mL) at 0° C. is added in one portion 1,1′-carbonyl diimidazole (4.8 g; 29.8 mmol; 1.2 eq) and the reaction mixture is stirred for 3 h at room temperature. A solution of dimethylamine (37.3 mL; 2 M; 74.6 mmol; 3 eq) in THF is added dropwise over 20 min and the reaction mixture is stirred at room temperature for 1 h. The solvent is removed under reduced pressure and the residue is diluted with EtOAc (100 mL) and the organic phase is washed with a 10% solution of NaHCO3 (30 mL). The white precipitate formed in the aqueous phase is filtered off, washed with water and dried under vacuum to afford 4.1 g (72%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 7.86 (d, J=8.3 Hz, 2H), 7.58 (d, J=8.3 Hz, 2H), 7.45 (s, 2H), 3.00 (s, 3H), 2.88 (s, 3H). HPLC (max plot) 99%; Rt 1.07 min. LC/MS: (ES+): 229.0.

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 1 h
  2. customThe solvent is removed under reduced pressure
  3. additionthe residue is diluted with EtOAc (100 mL)
  4. washthe organic phase is washed with a 10% solution of NaHCO3 (30 mL)
  5. customThe white precipitate formed in the aqueous phase
  6. filtrationis filtered off
  7. washwashed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-4f53dcb4a4344da08b4d8a6c7ba9f385
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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