Benzenesulfonamide, 3-amino- → HCID 4852487, compound

HRID 1669953Notes

Reaction equation

HRID 1669953 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.NC1C=CC=CC=1S(N)(=O)=O.Cl.[CH3:24][N:25]([CH2:27][C:28](Cl)=[O:29])[CH3:26].C(=O)(O)[O-].[Na+]>O.CC(C)=O>[CH3:24][N:25]([CH3:26])[CH2:27][C:28]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8](=[O:9])(=[O:10])[NH2:11])[CH:3]=1)=[O:29]

Participants

7

Reactant 4

HCID 7377Benzenesulfonamide, 3-amino-HCID 728942-AminobenzenesulfonamideHCID 516892Sodium BicarbonateHCID 139949912-(Dimethylamino)acetyl chloride hydrochloride

Product 1

HCID 4852487HCID 4852487, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A flask was charged with 3-aminobenzene sulfonamide (3.3 g, 19 mmol), and 20 mL of 1:1 acetone:H2O. The solution was stirred at room temperature until the aminobenzene sulfonamide had dissolved. The flask was then cooled in an ice bath and dimethylamino-acetyl chloride HCl (4.6 g, 29 mmol) was added. To the resulting slurry sodium bicarbonate (4.8 g, 57 mmol) was added over a 15 m period. After 30 min the reaction was removed from the ice bath and allowed to stir at room temperature for 15 h. The reaction mixture was then filtered and washed with methanol and acetonitrile. The filtrate was dried on a rotary evaporator to yield 2-(dimethylamino)-N-(3-sulfamoyl-phenyl)acetamide, which was submitted to the next step without further purification. MS (EI) m/z C10H15N3O3S: 258.0 (MH+).

Workup

  1. dissolutionhad dissolved
  2. temperatureThe flask was then cooled in an ice bath
  3. customAfter 30 min the reaction was removed from the ice bath
  4. filtrationThe reaction mixture was then filtered
  5. washwashed with methanol and acetonitrile
  6. customThe filtrate was dried on a rotary evaporator

Sources & evidence

ORD record
ord-a9945840feb94d8c97d4dae02bdacd79
Source dataset
uspto-grants-2011_08
Patent number
US07989622B2

Reaction notes

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