Water → 3-nitro-N-(1,3-thiazol-2-yl)benzenesulfonamide

HRID 2379343Notes

Reaction equation

HRID 2379343 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[N+:7]([C:10]1[CH:11]=[C:12]([S:16](Cl)(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1)([O-:9])=[O:8].[OH-].[Na+].O>N1C=CC=CC=1>[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[NH:1][S:16]([C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=1)(=[O:17])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 21552-AminothiazoleHCID 84763-Nitrobenzenesulfonyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 28624583-nitro-N-(1,3-thiazol-2-yl)benzenesulfonamideYield 87%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-aminothiazole (1 g, 10.5 mmol) in dry pyridine (3 ml) was added, portionwise, 3-nitrobenzenesulphonyl chloride (2.32 g, 10.5 mmol), maintaining the internal temperature below 55° C. After addition was complete, the mixture was heated at 100° C. for 75 min. 4M Sodium hydroxide solution (2.75 ml, 11 mmol) was then added dropwise and heating was continued for a further 5 min. After cooling, water (25 ml) was added and the precipitate was collected by filtration to afford the product (2.48 g, 87%) as a brown solid. mp 195° C. (dec.). 1H NMR (360 MHz, D6 -DMSO) δ 6.91 (1H, d, J=4.6 Hz), 7.31 (1H, d, J=4.5 Hz), 7.86 (1H, dd, J=8.0 and 8.1 Hz), 8.20-8.26 (1H, m), 8.40-8.45 ( 1H, m), 8.46-8.49 (1H, m), 13.00 (1H, brs).

Workup

  1. additionAfter addition
  2. temperatureheating
  3. temperatureAfter cooling
  4. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-864f10d12fad46d5944160c675aa989b
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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