5-Fluoro-o-tolyl Isothiocyanate → Methyl (2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl)acetate

HRID 1372638노트

반응식

HRID 1372638 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([N:8]=[C:9]=S)[CH:7]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:15][C:14]=1[OH:24]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([NH:8][C:9]2[O:24][C:14]3[CH:15]=[C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:17]=[CH:18][C:13]=3[N:12]=2)[CH:7]=1

참가 물질

4

반응물 2

HCID 5194435-Fluoro-o-tolyl IsothiocyanateHCID 17858854Methyl 2-(4-amino-3-hydroxyphenyl)acetate

생성물 1

HCID 58778736Methyl (2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl)acetate수율 46%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
70 °C

실험 절차

In methanol (50 ml), 5-fluoro-2-methylphenyl isothiocyanate (2.00 g, 12.0 mmol) was added to methyl 4-amino-3-hydroxyphenylacetate (2.17 g, 12.0 mmol) at room temperature. After stirring for 27 hours, mercuric oxide (yellow) (3.12 g, 14.4 mmol) was added to the reaction mixture and the resulting mixture was heated at 70° C. for 4 hours. After cooling to room temperature, the reaction mixture was filtered through Celite. The filtrate was washed with methanol. The filtrate was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from chloroform/ethyl acetate (10/1) eluate fractions, methyl (2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl)acetate (1.73 g, 46%) was obtained as a pale brown oil.

후처리

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered through Celite
  3. washThe filtrate was washed with methanol
  4. distillationThe filtrate was distilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by chromatography on a silica gel column, whereby from chloroform/ethyl acetate (10/1) eluate fractions

출처 및 근거

ORD 기록
ord-5f136369040e47248e568276b8621d6b
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157487B2

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