Ammonium Hydroxide → HCID 15233883, compound

HRID 2226863Notes

Reaction equation

HRID 2226863 reaction equation
[Cl:1][C:2]1[C:10]2[C:9]([S:11][CH:12]([CH3:14])[CH3:13])=[C:8]([C:15]([OH:17])=O)[S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)([N:20]1C=CN=C1)=O.[OH-].[NH4+]>C(#N)C>[Cl:1][C:2]1[C:10]2[C:9]([S:11][CH:12]([CH3:14])[CH3:13])=[C:8]([C:15]([NH2:20])=[O:17])[S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 18963772HCID 18963772, compound

Product 1

HCID 15233883HCID 15233883, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-chloro-3-[(1-methylethyl)thio]benzo[b]thiophene-2-carboxylic acid (0.43 g, 1.5 mmol) and 1,1'-carbonyldiimidazole (0.25 g, 1.5 mmol) in 5.0 mL of acetonitrile is stirred at reflux for 2 hours. The cooled reaction solution is added slowly to 20 mL of cold ammonium hydroxide solution. The precipitated solid is filtered, washed with water, and recrystallized from aqueous acetonitrile to give 0.15 g (35%) of product; mp=182°-184° C.

Workup

  1. temperatureat reflux for 2 hours
  2. customThe cooled reaction solution
  3. filtrationThe precipitated solid is filtered
  4. washwashed with water
  5. customrecrystallized from aqueous acetonitrile

Sources & evidence

ORD record
ord-ab16719b4cbb4c868ad78aa47820822b
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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