Hydrochloric Acid → HCID 59363804, compound

HRID 2189172Notes

Reaction equation

HRID 2189172 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[CH:7]=O.[OH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][C:11]=1[CH3:19].[OH-].[Na+].Cl>CCO>[OH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])/[CH:17]=[CH:7]/[C:6]2[S:5][CH:4]=[N:3][C:2]=2[CH3:1])=[CH:12][C:11]=1[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 701354'-Hydroxy-3'-methylacetophenoneHCID 5813394-Methylthiazole-5-carboxaldehyde

Product 1

HCID 59363804HCID 59363804, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Commerically available 4-methylthiazole-5-carbaldehyde (0.59 g, 4.6 mmol) and 4′-hydroxy-3′-methylacetophenone (0.7 g, 4.6 mmol) were dissolved in 10 mL of absolute EtOH. The solution was cooled with an ice-water bath, and NaOH (0.36 g, 9.0 mmol) was added. The reaction mixture was stirred for 18 h at room temperature. Upon completion, the reaction mixture was acidified to pH=4-5 with 1 M HCl. The resulting orange precipitate was filtered out, washed with an additional 5 mL of water, and dried under air. The resulting ((E)-1-(4-hydroxy-3-methylphenyl)-3-(4-methylthiazol-5-yl)prop-2-en-1-one (1.03 g, 87%) was submitted to the next step without further purification. MS (EI) for C14H13NO2S: 260 (MH+).

Workup

  1. temperatureThe solution was cooled with an ice-water bath
  2. filtrationThe resulting orange precipitate was filtered out
  3. washwashed with an additional 5 mL of water
  4. customdried under air
  5. customThe resulting ((E)-1-(4-hydroxy-3-methylphenyl)-3-(4-methylthiazol-5-yl)prop-2-en-1-one (1.03 g, 87%) was submitted to the next step without further purification

Sources & evidence

ORD record
ord-d400ba1375f24abf9adea556e69983cf
Source dataset
uspto-grants-2012_12
Patent number
US08324231B2

Reaction notes

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