Trimethyl orthoformate → 2-(4-Chloro-phenyl)-4-(2,2-dimethoxy-ethyl)-thiazole-5-carboxylic acid methyl ester

HRID 554839Notes

Reaction equation

HRID 554839 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[N:7][C:6]=1[CH2:17]C=O)=[O:4].[CH:20]([O:25][CH3:26])([O:23][CH3:24])OC>CO>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[N:7][C:6]=1[CH2:17][CH:20]([O:23][CH3:24])[O:25][CH3:26])=[O:4]

Participants

4

Reactant 2

HCID 9005Trimethyl orthoformateHCID 866400002-(4-Chloro-phenyl)-4-(2-oxo-ethyl)-thiazole-5-carboxylic acid methyl ester

Product 1

HCID 674611542-(4-Chloro-phenyl)-4-(2,2-dimethoxy-ethyl)-thiazole-5-carboxylic acid methyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Mix 2-(4-chloro-phenyl)-4-(2-oxo-ethyl)-thiazole-5-carboxylic acid methyl ester (96.4 g, 308 mmol), Dowex™ 50×8 ion exchange resin (33.3 g), and trimethyl orthoformate (147 mL) in MeOH (670 mL). Stir the slurry overnight at room temperature. Filter through a plug of diatomaceous earth and rinse with MeOH (3×300 mL). Stir the filtrate at 0° C. for 2 h and then concentrate to a volume of approximately 250 mL. Collect the solid by filtration, rinse with cold MeOH, and dry overnight at room temperature to obtain 88.2 g (84%) of the titled compound. ES/MS m/z (35Cl) 342.0 [M+1]+.

Workup

  1. filtrationFilter through a plug of diatomaceous earth
  2. washrinse with MeOH (3×300 mL)
  3. stirringStir the filtrate at 0° C. for 2 h
  4. concentrationconcentrate to a volume of approximately 250 mL
  5. customCollect the solid
  6. filtrationby filtration
  7. washrinse with cold MeOH
  8. customdry overnight at room temperature

Sources & evidence

ORD record
ord-5e5452b818f049deab3ea1f316a615dc
Source dataset
uspto-grants-2011_11
Patent number
US08049013B2

Reaction notes

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