Water → 4-(5-{3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-phenyl}-[1,3,4]thiadiazol-2-ylmethyl)-benzoic acid methyl ester

HRID 349452Notes

Reaction equation

HRID 349452 reaction equation
[CH3:1][O:2][C:3](=[O:36])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][NH:14][C:15](=O)[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[O:23][C:24]([C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=4)=[CH:25][N:26]=3)[CH:17]=2)=O)=[CH:6][CH:5]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:38].O>O1CCOCC1>[CH3:1][O:2][C:3](=[O:36])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[S:38][C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]4[O:23][C:24]([C:27]5[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=5)=[CH:25][N:26]=4)[CH:17]=3)=[N:14][N:13]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14817Phosphorus sulfide (P2S5)HCID 588048614-[2-(N'-{3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-benzoyl}-hydrazino)-2-oxo-ethyl]-benzoic Acid Methyl Ester

Product 1

HCID 588048824-(5-{3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-phenyl}-[1,3,4]thiadiazol-2-ylmethyl)-benzoic acid methyl esterYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 0.25 g (0.51 mmol) 4-[2-(N′-{3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-benzoyl}-hydrazino)-2-oxo-ethyl]-benzoic acid methyl ester from Preparation 8 in 10 mL dry dioxane was added P2S5 in one portion. The resulting mixture was warmed to 50° C. for 1 hour before cooling to room temperature and adding about 20 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 0.18 g (73%) desired product. Used directly in the procedure of Example B3 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-7b7aa2263f7d41a6a7670ed1d3a918a6
Source dataset
uspto-grants-2007_02
Patent number
US07179822B2

Reaction notes

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