Water → HCID 1239093, compound

HRID 857074Notes

Reaction equation

HRID 857074 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.O>N1C=CC=CC=1>[CH3:17][C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:24]([C:21]4[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=4)(=[O:26])=[O:25])=[CH:7][CH:6]=3)[S:9][C:10]=2[CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7087Dehydrothio-4-toluidineHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 1239093HCID 1239093, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To 2-(4-aminophenyl)-6-methylbenzothiazole (5 g, 20.8 mmol) in pyridine (60 mL) was added para-toluenesulphonyl chloride (5.953 g, 31.2 mmol, 1.5 eq.) in pyridine (40 mL). The reaction mixture was heated at reflux for 10 mins, then cooled and water (100 mL) added. The white precipitate formed was collected on a filter, washed with water and dried under vacuum to give N-[4-(6-methylbenzothiazol-2-yl)phenyl]-4-methylbenzenesulfonamide as a white solid. The yield was 8.091 g (99%).

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-16a165f2e5af4af4aaa5164037f34225
Source dataset
uspto-grants-2006_12
Patent number
US07144893B2

Reaction notes

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