Water → N-[(4-benzothiazol-2-yl)phenyl]-4-methylbenzenesulfonamide

HRID 857072

Reaction equation

HRID 857072 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.O>N1C=CC=CC=1>[S:9]1[C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=[C:8]1[C:5]1[CH:4]=[CH:3][C:2]([NH:1][S:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=2)(=[O:25])=[O:24])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 2344752-(4-Aminophenyl)benzothiazole

Product 1

HCID 4380499N-[(4-benzothiazol-2-yl)phenyl]-4-methylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To 2-(4-aminophenyl)-benzothiazole (0.5 g, 2.2 mmol) in pyridine (6 mL) was added para-toluenesulphonyl chloride (0.506 g, 2.7 mmol, 1.5 equiv.) in pyridine (4 mL). The reaction mixture was heated at reflux for 10 mins, then cooled and water (10 mL) added. The white precipitate formed was collected on a filter, washed with water and dried under vacuum to give N-[(4-benzothiazol-2-yl)phenyl]-4-methylbenzenesulfonamide as a white solid. The yield was 0.807 g (96%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 10 mins
  3. temperaturecooled
  4. customThe white precipitate formed
  5. customwas collected on a filter
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-72529ed308ac452380d4c4070f272ff0
Source dataset
uspto-grants-2006_12
Patent number
US07144893B2

Linked notes

Loading…