4-Methoxybenzaldehyde → 219806-93-6

HRID 619122Notes

Reaction equation

HRID 619122 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[C:11]([CH2:14][C:15](=O)[CH3:16])(=[O:13])[CH3:12].[NH2:18][C:19]([NH2:21])=[S:20]>C(O)C.Cl>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]2[C:14]([C:11](=[O:13])[CH3:12])=[C:15]([CH3:16])[NH:21][C:19](=[S:20])[NH:18]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 312444-MethoxybenzaldehydeHCID 31261AcetylacetoneHCID 2723790Thiourea

Product 1

HCID 3097577219806-93-6Yield 22.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

A solution of 12.1 ml (0.1 mol) of 4-methoxybenzaldehyde, 10.3 ml (0.1 mol) of acetylacetone and 9.13 g (0.12 mol) of thiourea in 30 ml of ethanol was treated with 10 drops of conc. hydrochloric acid and boiled under reflux while stirring for 4 h. The reaction mixture was concentrated and the residue was purified by column chromatography on silica gel (dichloromethane-methanol 98:2). Subsequent crystallization from ethanol gave 6.2 g (22%) of (RS)-1-[4-(4-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]ethanone as a red-brown solid with m.p. 175° C.

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by column chromatography on silica gel (dichloromethane-methanol 98:2)
  4. customSubsequent crystallization from ethanol

Sources & evidence

ORD record
ord-ae6d3ac0b90e490fbdab9830f1b5292a
Source dataset
uspto-grants-1999_09
Patent number
US05958931

Reaction notes

Loading…