Benzenesulfonamide, 3-amino- → HCID 59353037, compound

HRID 1914715Notes

Reaction equation

HRID 1914715 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:3]=1.[CH2:12]([O:19][CH2:20][C:21](Cl)=[O:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+]>CC(C)=O.O>[NH2:11][S:8]([C:4]1[CH:3]=[C:2]([NH:1][C:21](=[O:22])[CH2:20][O:19][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=[CH:6][CH:5]=1)(=[O:9])=[O:10]

Participants

6

Reactant 3

HCID 7377Benzenesulfonamide, 3-amino-HCID 177085Benzyloxyacetyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 59353037HCID 59353037, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A suspension of 1-aminobenzene-3-sulfonamide (1 g; 5.8 mmol; 1 eq) in a mixture of acetone (10 mL) and water (10 mL) is stirred at room temperature until complete dissolution. Benzyloxyacetyl chloride (1.4 mL; 8.7 mmol; 1.5 eq) is added at 0° C. followed by the addition of NaHCO3 (1.4 g) over 15 min. After 30 min, the reaction mixture is allowed to stir at room temperature for 2 h. The reaction mixture is then filtered off and the solid residue is washed with MeOH and ACN. The filtrate is concentrated to dryness, affording 1.8 g (97%) of the title compound as a brown foam. 1H NMR (DMSO-d6) δ 8.25 (br s, 1H), 7.81-7.75 (m, 1H), 7.55-7.48 (m, 2H), 7.42-7.28 (m, 8H), 4.62 (s, 2H), 4.13 (s, 2H). HPLC (max plot) 91%; Rt 2.53 min. UPLC/MS: (ES+) 321.2; (ES−) 319.2.

Workup

  1. stirringto stir at room temperature for 2 h
  2. filtrationThe reaction mixture is then filtered off
  3. washthe solid residue is washed with MeOH and ACN
  4. concentrationThe filtrate is concentrated to dryness

Sources & evidence

ORD record
ord-9b88c873708541beb6ce4d66b3a98439
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

Loading…