Hydrochloric Acid → HCID 88184493, compound

HRID 2297737Notes

Reaction equation

HRID 2297737 reaction equation
[Na].C[SH:3].Br[C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=O.Cl.[C:14]1(P(=CC(OC)=O)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:19]=CC=C[CH:15]=1.CN(C)[CH:40]=[O:41]>C(OCC)(=O)C>[CH3:7][C:6]1[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=1[CH:15]=[CH:14][C:19]([O:41][CH3:40])=[S:3]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 811292-BromobenzaldehydeHCID 45051789Methylmercaptan sodium

Product 1

HCID 88184493HCID 88184493, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methanethiol sodium salt (4.0 g, 52 mmol) was added to a solution (70 mL) of 2-bromobenzaldehyde (9.25 g, 50 mmol) in N,N-dimethylformamide, followed by reflux for 2 hours. Next, the reaction solution was added to dilute hydrochloric acid (0.5 mol/L) under ice-cooling to neutralize the reaction solution, and the mixture was then extracted with ethyl acetate. After the extract was washed with a saturated aqueous solution of sodium bicarbonate and with a saturated brine and then dried over sodium sulfate, the solvent was evaporated under reduced pressure. The obtained crude 2-methylthiobenzaldehyde was dissolved in ethyl acetate (30 mL), and methyl triphenylphosphoranylideneacetate (16.7 g, 50 mmol) was added thereto, followed by stirring at room temperature for 12 hours. Thereafter, the solvent was evaporated under reduced pressure, and the residue was powdered with hexane to give methyl o-methylthiocinnamate (5.43 g, yield 51%).

Workup

  1. temperatureby reflux for 2 hours
  2. temperaturecooling
  3. extractionthe mixture was then extracted with ethyl acetate
  4. washAfter the extract was washed with a saturated aqueous solution of sodium bicarbonate and with a saturated brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained crude 2-methylthiobenzaldehyde
  8. customThereafter, the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7cd97bcd509b400a85d4a960d99c90fd
Source dataset
uspto-grants-2002_12
Patent number
US06492392B1

Reaction notes

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