Benzo(d)thiazol-2-amine → Benzamide, N-2-benzothiazolyl-4-butyl-

HRID 2085363Notes

Reaction equation

HRID 2085363 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.[CH2:11]([C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1)[CH2:12][CH2:13][CH3:14].[OH-].[Na+]>C(Cl)Cl.N1C=CC=CC=1>[CH2:11]([C:15]1[CH:16]=[CH:17][C:18]([C:19]([NH:1][C:2]2[S:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)=[O:20])=[CH:22][CH:23]=1)[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 8706Benzo(d)thiazol-2-amineHCID 14798Sodium HydroxideHCID 1200494-Butylbenzoyl chloride

Product 1

HCID 3939072Benzamide, N-2-benzothiazolyl-4-butyl-

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-amino-1,3-benzthiazole (40 mg, 0.27 mmol) in methylene chloride (1 ml) and pyridine (100 μl) was treated with 4-n-butylbenzoyl chloride and stirred at 25° C. for 30 minutes. After this time, the reaction was treated with NaOH (0.5 ml, 5.0 M) and the resulting mixture stirred overnight. The resulting precipitate was collected by filtration and recrystallized from water to give 2-(4-n-butylbenzamido)-1,3-benzthiazole as pale yellow needles. (47 mg, 53%)

Workup

  1. stirringthe resulting mixture stirred overnight
  2. filtrationThe resulting precipitate was collected by filtration
  3. customrecrystallized from water

Sources & evidence

ORD record
ord-ba73110823a842b1892def412eafc835
Source dataset
uspto-grants-2004_04
Patent number
US06720344B2

Reaction notes

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