Methanol → HCID 178503459, compound

HRID 271059Notes

Reaction equation

HRID 271059 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([C:6](=[CH:12][O:13]CC)[C:7](OCC)=O)=[O:5].[NH2:20][C:21]([NH2:23])=[S:22].[CH3:24][O-].[Na+].CO.IC>C(O)C.O>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([C:6]1[C:12]([OH:13])=[N:20][C:21]([S:22][CH3:24])=[N:23][CH:7]=1)=[O:5]

Participants

8

Reactant 5

HCID 887MethanolHCID 6328Methyl iodideHCID 2723790ThioureaHCID 10942334Sodium MethoxideHCID 85437380HCID 85437380, compound

Product 1

HCID 178503459HCID 178503459, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent3×

Procedure

To a solution of 2-(2-chlorobenzoyl)-3-ethoxyacrylic acid, ethyl ester (23.9 g, 23.9 mmol) in absolute ethanol (80 mL) was added thiourea (7.14 g, 23.9 mmol), followed by a solution of 25% sodium methoxide in methanol (20.4 mL, 89.3 mmol). The reaction mixture was heated to reflux for four hours, and then stirred at room temperature over night. The resulting mixture was diluted with water (50 mL) and then treated with iodomethane (11.99 mL, 21.5 mmol). The material was warmed to 40° C. and stirred for three hours. Water (10 mL) was added and the material allowed to cool to room temperature over 10 minutes. Another 50 mL of water was added and the product slowly crystallized out of the resulting solution. The product was collected by filtration (18.72 g, (M+H)+=281).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for four hours
  3. temperatureThe material was warmed to 40° C.
  4. stirringstirred for three hours
  5. temperatureto cool to room temperature over 10 minutes
  6. customthe product slowly crystallized out of the resulting solution
  7. filtrationThe product was collected by filtration (18.72 g, (M+H)+=281)

Sources & evidence

ORD record
ord-ed529d9562e54b089eaaa44bf358e167
Source dataset
uspto-grants-2008_11
Patent number
US07452880B2

Reaction notes

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