Water → 3-[5-(4-Methoxy-phenyl)-thiazol-2-yl]-benzoic acid methyl ester

HRID 349440Notes

Reaction equation

HRID 349440 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:23]=[CH:22][CH:21]=[C:6]([C:7]([NH:9][CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=O)=O)[CH:5]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:26].O>O1CCOCC1>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:23]=[CH:22][CH:21]=[C:6]([C:7]2[S:26][C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[CH:10][N:9]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14817Phosphorus sulfide (P2S5)HCID 58804856N-[2-(4-Methoxy-phenyl)-2-oxo-ethyl]-isophthalamic Acid Methylester

Product 1

HCID 588048543-[5-(4-Methoxy-phenyl)-thiazol-2-yl]-benzoic acid methyl esterYield 100.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 1.4 g (4.3 mmol) N-[2-(4-Methoxy-phenyl)-2-oxo-ethyl]-isophthalamic acid methylester from Preparation 2 in 30 mL of dry dioxane was added 1.1 g (5.2 mmol) of P2S5 in one portion. The resulting mixture was warmed to 50° C. for 1 hour before cooling to room temperature and adding about 60 ml water. Stirred 2 hours and then filtered off solid product. Triturated in hot MeOH and filtered. Dissolved in THF and filtered through a plug of flash silica gel with THF eluent. Concentration gave 1.4 g (100%) of desired product. Used directly in the procedure of Preparation 11 without characterization.

Workup

  1. temperaturebefore cooling to room temperature
  2. filtrationfiltered off solid product
  3. customTriturated in hot MeOH
  4. filtrationfiltered
  5. dissolutionDissolved in THF
  6. filtrationfiltered through a plug of flash silica gel with THF eluent
  7. concentrationConcentration

Sources & evidence

ORD record
ord-297f83240fbb4095ad944ba111603661
Source dataset
uspto-grants-2007_02
Patent number
US07179822B2

Reaction notes

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