Triethylamine → 2-Fluoro-5-(4-methylbenzoxazol-2-yl)nitrobenzene

HRID 74213노트

반응식

HRID 74213 반응식
[F:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)C(O)=O.S(Cl)(Cl)=O.[OH:18][C:19]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:20]=1[NH2:21].[CH2:27](N(CC)CC)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C=O)C.C1(C)C=CC=CC=1.O.O1CCCC1>[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:27]2[O:18][C:19]3[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:20]=3[N:21]=2)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

참가 물질

10

반응물 5

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 521998p-Toluenesulfonic acid monohydrateHCID 30141382-Amino-m-cresolHCID 189159203-Fluoro-2-nitrobenzoic acid

생성물 1

HCID 674986872-Fluoro-5-(4-methylbenzoxazol-2-yl)nitrobenzene수율 37%

시약·촉매·용매 4

HCID 6228Dimethylformamide촉매HCID 962Water용매2회HCID 1140Toluene용매2회HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of 3-fluoro-2-nitrobenzoic acid (1.00 g, 5.40 mmol) and DMF (1 drop) in toluene (10 mL) was added thionyl chloride (0.78 g, 6.56 mmol) and this was stirred at reflux for 3 hours. After the reaction was complete, concentration at reduced pressure gave a residue that was added to 2-hydroxy-6-methylaniline (0.66 g, 5.4 mmol), triethylamine (0.66 g, 6.5 mmol) and tetrahydrofuran (5 mL), and this was stirred at room temperature for 3 hours. After the reaction was complete, water (50 mL) was added, and this was extracted with ethyl acetate. After the organic layer was dried over anhydrous sodium sulfate, filtration and concentration gave crystals that were added to toluene (20 mL), to which p-toluenesulfonic acid hydrate (1.14 g, 5.99 mmol) was next added and this was stirred at reflux for 2 hours. After concentration of the solvent at reduced pressure, water (5 mL) was added, after which this was extracted with ethyl acetate. The organic layer obtained was dried over anhydrous sodium sulfate, after which it was filtered and concentrated to yield the title compound (0.50 g, 37% yield) as a light brown solid.

후처리

  1. temperatureat reflux for 3 hours
  2. concentrationconcentration at reduced pressure
  3. customgave a residue that
  4. stirringthis was stirred at room temperature for 3 hours
  5. extractionthis was extracted with ethyl acetate
  6. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate, filtration and concentration
  7. customgave crystals that
  8. additionwas next added
  9. stirringthis was stirred
  10. temperatureat reflux for 2 hours
  11. extractionafter which this was extracted with ethyl acetate
  12. customThe organic layer obtained
  13. dry with materialwas dried over anhydrous sodium sulfate
  14. filtrationafter which it was filtered
  15. concentrationconcentrated

출처 및 근거

ORD 기록
ord-139176261c2c4472bb24c540702aa958
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

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