2-Methoxybenzaldehyde → 2-(2-Methoxyphenyl)-5-methyl-2,5-dihydro-1,3-thiazol-4-ol

HRID 1388899Notes

Reaction equation

HRID 1388899 reaction equation
[CH:1](=O)[C:2]1[C:3]([O:8][CH3:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.[SH:11][CH:12]([CH3:18])[C:13](OCC)=[O:14].C(=O)([O-])[O-].[NH4+:23].[NH4+]>C1(C)C=CC=CC=1>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:1]1[NH:23][C:13](=[O:14])[CH:12]([CH3:18])[S:11]1

Participants

5

Reactant 3

HCID 86582-MethoxybenzaldehydeHCID 517111Ammonium CarbonateHCID 519709Ethyl 2-mercaptopropionate

Product 1

HCID 30680342-(2-Methoxyphenyl)-5-methyl-2,5-dihydro-1,3-thiazol-4-olYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 13.6 g of o-anisaldehyde, 13.4 g of ethyl 2-mercaptopropionate and 6 g of ammonium carbonate in 250 ml of toluene was refluxed at 110° C. for 2 hours in a flask provided with a Dean-Stark apparatus while removing the distilled water. The crystals which separated out after leaving the reaction mixture for a night were collected by filtering and recrystallized from hot benzene to obtain the object, colourless prisms melting at 187° to 187.5° C. in an amount of 21 g corresponding to a yield of 94%.

Workup

  1. customprovided with a Dean-Stark apparatus
  2. customwhile removing the distilled water
  3. customThe crystals which separated out
  4. customafter leaving the reaction mixture for a night
  5. customwere collected
  6. filtrationby filtering
  7. customrecrystallized from hot benzene

Sources & evidence

ORD record
ord-b5ae663be7794d1b8623c19425ff973c
Source dataset
uspto-grants-1984_02
Patent number
US04434172

Reaction notes

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