4-Methyl-5-(2-hydroxyethyl)thiazole → 4-[2-(4-Methyl-1,3-thiazol-5-yl)ethoxy]-2-nitroaniline

HRID 272697

반응식

HRID 272697 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][C:13]1[N:14]=[CH:15][S:16][C:17]=1[CH2:18][CH2:19]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[CH3:12][C:13]1[N:14]=[CH:15][S:16][C:17]=1[CH2:18][CH2:19][O:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

참가 물질

6

반응물 4

HCID 11364-Methyl-5-(2-hydroxyethyl)thiazoleHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 37588824-Amino-3-Nitrophenol

생성물 1

HCID 692199834-[2-(4-Methyl-1,3-thiazol-5-yl)ethoxy]-2-nitroaniline수율 86.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 4-amino-3-nitrophenol (386 mg, 2.5 mmol), 2-(4-methyl-1,3-thiazol-5-yl)ethanol (0.299 mL, 2.5 mmol), polymer supported triphenylphosphine (1.25 g, 3 mmol/g, 3.75 mmol), and di-tert-butyl azodicarboxylate (864 mg, 3.75 mmol) in THF (10 mL) was stirred at room temperature for 16 hours. Filtered through Celite and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 1:1 hexanes/ethyl acetate to provide 602 mg (86%) of the desired product. MS (DCI) m/e 279 (M+H)+, 1H NMR (300 MHz, DMSO-d6): □ 8.83 (s, 1H), 7.37 (d, J=3.05 Hz, 1H), 7.25 (s, 2H), 7.16 (dd, J=8.99, 2.88 Hz, 1H), 7.01 (s, 1H), 4.10 (t, J=6.27 Hz, 2H), 3.19 (t, J=6.27 Hz, 2H), 2.35 (s, 3H).

후처리

  1. filtrationFiltered through Celite
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by flash column chromatography on silica gel with 1:1 hexanes/ethyl acetate

출처 및 근거

ORD 기록
ord-409df72e33cf45d8a976a3b4eefceee5
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456169B2

연결된 노트

불러오는 중…