2-Chlorobenzaldehyde → HCID 8424963, compound

HRID 884644Notes

Reaction equation

HRID 884644 reaction equation
[C:1]([C:4]1[S:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=O.[OH-].[Na+]>CO>[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1/[CH:15]=[CH:2]/[C:1]([C:4]1[S:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 37427275-Acetylthiophene-2-carboxylic acid

Product 1

HCID 8424963HCID 8424963, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Commercially available 5-acetylthiophene-2-carboxylic acid (1.0 g, 5.9 mmol) and commercially available 2-chlorobenzaldehyde (670 uL, 5.9 mmol) were dissolved in 30 mL of methanol. The solution was cooled in an ice bath and solid sodium hydroxide (940 mg, 23.5 mmol) was added. The cold bath was removed and the reaction was stirred for 2 hours at room temperature. The reaction was then heated at 50° C. for another 2 hours. Concentrated HCl was added to lower the pH to 3. The reaction was filtered, washed with water and air dried to give 1.5 g of product. MS (EI) for C14H9ClO3S: 292 (MH+).

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. customThe cold bath was removed
  3. temperatureThe reaction was then heated at 50° C. for another 2 hours
  4. additionConcentrated HCl was added
  5. filtrationThe reaction was filtered
  6. washwashed with water and air
  7. customdried

Sources & evidence

ORD record
ord-6a9ac21103e94a78b2f240fbbce4e023
Source dataset
uspto-grants-2012_08
Patent number
US08242129B2

Reaction notes

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