Hydrochloric Acid → N-(1,3-benzothiazol-2-yl)-2,4-dimethoxybenzamide

HRID 2085362Notes

Reaction equation

HRID 2085362 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.[CH3:11][O:12][C:13]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16].Cl>C(Cl)Cl.N1C=CC=CC=1>[O:12]([C:13]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:14]=1[C:15]([NH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1)=[O:16])[CH3:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8706Benzo(d)thiazol-2-amineHCID 27347192,4-Dimethoxybenzoyl chloride

Product 1

HCID 788928N-(1,3-benzothiazol-2-yl)-2,4-dimethoxybenzamideYield 80%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-amino-1,3-benzthiazole (700 mg, 4.7 mmol) in methylene chloride (20 ml) and pyridine (800 μl) was treated with 2,4-dimethoxybenzoyl chloride and stirred at 25° C. for 30 minutes. After this time, the reaction was treated with HCl (10 ml of 5 wt %) and the resulting precipitated collected by filtration. The solid was recrystallized from methanol to give 2-(2,4-dimethoxylbenzamido)-1,3-benzthiazole as colorless needles. (1.185 mg, 80% yield)

Workup

  1. customthe resulting precipitated
  2. filtrationcollected by filtration
  3. customThe solid was recrystallized from methanol

Sources & evidence

ORD record
ord-e0f53ac0ee5e4284bbd2b6ffb654b9f9
Source dataset
uspto-grants-2004_04
Patent number
US06720344B2

Reaction notes

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