1-Naphthyl Isothiocyanate → Methyl (2-(1-naphthylamino)-7-fluoro-6-benzoxazolyl)acetate

HRID 1372657노트

반응식

HRID 1372657 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:4]([F:13])[C:3]=1[OH:14].[C:15]1([N:25]=[C:26]=S)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1>CO>[C:15]1([NH:25][C:26]2[O:14][C:3]3[C:4]([F:13])=[C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:7][C:2]=3[N:1]=2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1

참가 물질

4

반응물 2

HCID 110801-Naphthyl IsothiocyanateHCID 17859032Methyl (4-amino-2-fluoro-3-hydroxyphenyl)acetate

생성물 1

HCID 58779085Methyl (2-(1-naphthylamino)-7-fluoro-6-benzoxazolyl)acetate수율 81%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Methyl (4-amino-2-fluoro-3-hydroxyphenyl)acetate (996 mg, 5.00 mmol) was dissolved in methanol (50 ml). To the resulting solution was added 1-naphthyl isothiocyanate (926 mg, 5.00 mmol). After the resulting mixture was stirred at room temperature for 2 days, mercuric oxide (yellow) (1.08 g, 5.00 mmol) was added thereto. The mixture was stirred at 70° C. for 3.5 hours. After cooling to room temperature, the reaction mixture was filtered through Celite and washed with methanol. The filtrate was distilled under reduced pressure to remove the solvent. The crude crystals thus obtained were recrystallized from chloroform/n-hexane to give methyl (2-(1-naphthylamino)-7-fluoro-6-benzoxazolyl)acetate (1.41 g, 81%) as a pale gray crystalline powder.

후처리

  1. stirringThe mixture was stirred at 70° C. for 3.5 hours
  2. temperatureAfter cooling to room temperature
  3. filtrationthe reaction mixture was filtered through Celite
  4. washwashed with methanol
  5. distillationThe filtrate was distilled under reduced pressure
  6. customto remove the solvent
  7. customThe crude crystals thus obtained
  8. customwere recrystallized from chloroform/n-hexane

출처 및 근거

ORD 기록
ord-10e2046941034800b51ad2d2239cb5d3
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157487B2

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