4-Bromophenyl isothiocyanate → N-(4-Bromophenyl)-5-(trifluoromethyl)-1,3-benzoxazol-2-amine

HRID 9589

반응식

HRID 9589 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[OH:12].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=S)=[CH:16][CH:15]=1>C(O)C>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[O:12][C:3]3[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=3[N:1]=2)=[CH:16][CH:15]=1

참가 물질

4

반응물 2

HCID 161334-Bromophenyl isothiocyanateHCID 1202462-Amino-4-(trifluoromethyl)phenol

생성물 1

HCID 9924878N-(4-Bromophenyl)-5-(trifluoromethyl)-1,3-benzoxazol-2-amine수율 62.6%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

2-Amino-4-(trifluoromethyl)phenol (250 mg, 1.41 mmol) and 1-bromo-4-isothio-cyanatobenzene (302 mg, 1.41 mmol) were stirred in ethyl alcohol at ambient temperature for 18 h. The flask was charged with 1-[3-(dimethylamino)propyl]-3-ethylcarhodiimide hydrochloride (EDCI) (405 mg, 2.12 mmol), and the mixture was stirred for 2 h before being heated at reflux overnight. The reaction was allowed to cool to rt and was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with 2 N aqueous hydrochloric acid solution and water, dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with 85:15 hexanes/ethyl acetate to provide the title compound (315 mg, 62%). LC-MS m/z 357.1 (MH+), retention time 4.20 minutes.

후처리

  1. temperaturebefore being heated
  2. temperatureat reflux overnight
  3. concentrationwas concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with 2 N aqueous hydrochloric acid solution and water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel
  9. washeluting with 85:15 hexanes/ethyl acetate

출처 및 근거

ORD 기록
ord-a7d2367f51754c8a9d86866ac0fbbed9
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091228B2

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