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

HRID 460027노트

반응식

HRID 460027 반응식
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]

참가 물질

7

반응물 4

HCID 14812Phosphorus oxide (P4O10)HCID 516892Sodium BicarbonateHCID 3022879Ethyl 2-(2-methylphenoxy)acetateHCID 17972178[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-acetic acid2회

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6395Methanesulfonic Acid용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-49e54eb66b014b139ea23b4c48bc5329
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196107B2

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