Ammonium Hydroxide → 3-Chloro-5-methoxybenzo[b]thiophene-2-carboxamide

HRID 2226850Notes

Reaction equation

HRID 2226850 reaction equation
[Cl:1][C:2]1[C:3]2[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:4]=2[S:5][C:6]=1[C:7](Cl)=[O:8].[NH4+:16].[OH-]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]2[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:4]=2[S:5][C:6]=1[C:7]([NH2:16])=[O:8]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 101991093-Chloro-5-methoxybenzo[b]thiophene-2-carbonyl chloride

Product 1

HCID 106815953-Chloro-5-methoxybenzo[b]thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 3-chloro-5-methoxybenzo[b]thiophene-2-carbonyl chloride (1.52 g, 5.82 mmol) [Connor D. T., et al., J. Med. Chem. 35, 935 (1992)] in 80 mL of toluene at 50° C. is added dropwise 10 mL of aqueous NH4OH. The resulting precipitate is collected by filtration and recrystallized from methanol to provide 3-chloro-5-methoxybenzo[b]thiophene2-carboxamide; mp=220°-222° C.

Workup

  1. filtrationThe resulting precipitate is collected by filtration
  2. customrecrystallized from methanol

Sources & evidence

ORD record
ord-abee970752414950a23fc988f3a26d63
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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