4-Toluenesulfonyl chloride → HCID 178427428, compound

HRID 1819742Notes

Reaction equation

HRID 1819742 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>N1C=CC=CC=1>[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[NH:6][C:2]1=[N:1][S:17]([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 8706Benzo(d)thiazol-2-amine

Product 1

HCID 178427428HCID 178427428, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-aminobenzothiazole (1.018 g, 6.78 mmol) in dry pyridine (4 mL) was added portion wise, p-toluene sulfonyl chloride (1.42 g, 7.48 mmol). The solution turned yellow upon addition. After 5 minutes of stirring at rt, the mixture was heated (70-80° C.) for 5 minutes. The mixture was poured on a bed of ice and the resulting precipitate was filtered off and dried overnight in a dessicator under vacuum to give a yellow powder in 93% yield: mp 246-249° C.; 1H-NMR (DMSO-d6) 2.36 (s, 3H), 7.26, (dt, 1H), 7.30 (d, 1H), 7.37 (d, 2H), 7.40 (dt, 1H), 7.75 (d, 2H), 7.81 (d, 1H); Anal. (C14H12N2O2S2) C, H, N.

Workup

  1. additionThe solution turned yellow upon addition
  2. temperaturethe mixture was heated (70-80° C.) for 5 minutes
  3. additionThe mixture was poured on a bed of ice
  4. filtrationthe resulting precipitate was filtered off
  5. customdried overnight in a dessicator under vacuum
  6. customto give a yellow powder in 93% yield

Sources & evidence

ORD record
ord-ed4775ca390840b1b1a66683237e27d5
Source dataset
uspto-grants-2009_10
Patent number
US07601846B2

Reaction notes

Loading…