Acetic Anhydride → HCID 21942934, compound

HRID 2216429Notes

Reaction equation

HRID 2216429 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=O.[NH2:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[SH:20].[C:21](OC(=O)C)(=[O:23])[CH3:22]>CO>[C:21]([N:12]1[C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[S:20][CH:4]1[C:3]1[CH:6]=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:2]=1[OH:1])(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 120002-Amino-4-chlorobenzenethiolHCID 956952-Hydroxy-5-methoxybenzaldehyde

Product 1

HCID 21942934HCID 21942934, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2-hydroxy-5-methoxybenzaldehyde (10.0 g, 65.7 mmol) in methanol (20 ml) was added to a solution of 2-amino-4-chlorothiophenol (10.5 g, 65.7 mmol) in methanol (20 ml) under a nitrogen stream at room temperature, the mixture was stirred at room temperature for 50 minutes, and then the precipitated crystals were filtered off. Acetic anhydride (20 ml, 212 mmol) was added to the obtained crystals, the mixture was stirred at room temperature overnight, and then the reaction mixture was concentrated under reduced pressure. Methanol (60 ml), water (10 ml) and potassium carbonate (5.0 g) were added to the residue, the whole was stirred at room temperature overnight, and then the reaction mixture was concentrated under reduced pressure. Ethyl acetate (300 ml) and 1 N-hydrochloric acid (200 ml) were added to the residue, and the whole was extracted. The organic layer was washed with saturated brine (150 ml), dehydrated with anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=3/1) to give 7.7 g (60%) of the target compound.

Workup

  1. filtrationthe precipitated crystals were filtered off
  2. stirringthe mixture was stirred at room temperature overnight
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. additionMethanol (60 ml), water (10 ml) and potassium carbonate (5.0 g) were added to the residue
  5. stirringthe whole was stirred at room temperature overnight
  6. concentrationthe reaction mixture was concentrated under reduced pressure
  7. additionEthyl acetate (300 ml) and 1 N-hydrochloric acid (200 ml) were added to the residue
  8. extractionthe whole was extracted
  9. washThe organic layer was washed with saturated brine (150 ml)
  10. filtrationfiltered
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-b4f3b2959c364c26ae2c61c78179bf11
Source dataset
uspto-grants-2006_09
Patent number
US07112598B2

Reaction notes

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