Phosphorus oxide (P4O10) → Ethyl [2-methyl-4-({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}acetyl)phenoxy]acetate

HRID 460027Notes

Reaction equation

HRID 460027 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:15][C:16]1[N:17]=[C:18]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)[S:19][C:20]=1[CH2:21][C:22]([OH:24])=O.[CH3:35][C:36]1[CH:48]=[CH:47][CH:46]=[CH:45][C:37]=1[O:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41].C(=O)(O)[O-].[Na+]>CS(O)(=O)=O.O>[CH3:35][C:36]1[CH:48]=[C:47]([C:22](=[O:24])[CH2:21][C:20]2[S:19][C:18]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)=[N:17][C:16]=2[CH3:15])[CH:46]=[CH:45][C:37]=1[O:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41]

Participants

7

Reactant 4

HCID 14812Phosphorus oxide (P4O10)HCID 516892Sodium BicarbonateHCID 3022879Ethyl 2-(2-methylphenoxy)acetateHCID 17972178[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-acetic acid2×

Product 1

HCID 58824797Ethyl [2-methyl-4-({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}acetyl)phenoxy]acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
60 °C

Procedure

A well stirred suspension of phosphorus pentoxide (0.92 g) in methane sulfonic acid (6.5 ml) under nitrogen was heated to 60° C. until a clear solution formed. The mixture was then allowed to cool to room temperature prior to addition of {4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}acetic acid (intermediate 14, 0.98 g) and ethyl (2-methylphenoxy)acetate (0.49 ml). The mixture was heated to 60° C. for 90 minutes, after cooling to room temperature the reaction mixture was poured onto iced water (100 ml) and the acidic suspension basified by cautious addition of solid sodium bicarbonate. The product was extracted into ethyl acetate and the combined organic extracts dried (magnesium sulfate) filtered and evaporated. Purification by flash column chromatography using ethyl acetate:cyclohexane (1:9) as eluent gave title compound as a pale yellow solid.

Workup

  1. customformed
  2. temperatureto cool to room temperature
  3. temperatureThe mixture was heated to 60° C. for 90 minutes
  4. temperatureafter cooling to room temperature the reaction mixture
  5. extractionThe product was extracted into ethyl acetate
  6. dry with materialthe combined organic extracts dried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated
  9. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-49e54eb66b014b139ea23b4c48bc5329
Source dataset
uspto-grants-2007_03
Patent number
US07196107B2

Reaction notes

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