Hydrochloric Acid → 3-amino-N-(1,3-thiazol-2-yl)benzene-1-sulfonamide

HRID 2379344Notes

Reaction equation

HRID 2379344 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=1)(=[O:9])=[O:8].Cl>C(O)C.[Pd].O>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=1)(=[O:9])=[O:8]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 28624583-nitro-N-(1,3-thiazol-2-yl)benzenesulfonamide

Product 1

HCID 167883753-amino-N-(1,3-thiazol-2-yl)benzene-1-sulfonamideYield 76%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 1-(thiazol-2-ylaminosulphonyl )-3-nitrobenzene (0.5 g, 1.8 mmol) in ethanol (50 ml) was added 10% palladium on carbon. (0.25 g, 50% (w/w)) in water (2 ml) and 5M hydrochloric acid (1 ml, 5 mmol). The mixture was hydrogenated at 45 psi for 3 h. The catalyst was filtered off and washed with ethanol. The solvents were evaporated in vacuo and the residue chromatographed on silica gel using 10% methanol in dichloromethane as the eluant to afford the product (0.34 g, 76%) as a pale yellow solid. mp 187°-190° C. 1H NMR (360 MHz, D6 -DMSO) δ 5.49 (2H, brs), 6.66-6.73 (1H, m), 6.80 (1H, d, J=4.6 Hz), 6.85-6.90 (1H, m), 6.98-7.02 (1H, m), 7.11 (1H, dd, J=7.9 and 7.9 Hz), 7.22 (1H, d, J=4.7 Hz), 12.59 (1H, brs).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethanol
  3. customThe solvents were evaporated in vacuo
  4. customthe residue chromatographed on silica gel using 10% methanol in dichloromethane as the eluant

Sources & evidence

ORD record
ord-3e34b93c770041b3838f816c6fdae767
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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