Water → 2-Chloro-4-methoxyphenoxy-1,3-thiazole

HRID 404896노트

반응식

HRID 404896 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[OH:10].C([O-])([O-])=O.[K+].[K+].Br[C:18]1[S:19][CH:20]=[CH:21][N:22]=1.O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[O:10][C:18]1[S:19][CH:20]=[CH:21][N:22]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 874592-Chloro-4-methoxyphenol

생성물 1

HCID 694346862-Chloro-4-methoxyphenoxy-1,3-thiazole수율 81%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
150 °C

실험 절차

To a suspension of 2-chloro-4-methoxyphenol (10 g, 63 mmol) and K2CO3 (9.7 g, 69.4 mmol) in N,N-dimethyl formamide (120 mL) was added 2-bromothiazole (11.4 g, 69.4 mmol). The suspension was heated at 150° C. for 4 hours, cooled to ambient temperature, and poured into water (1000 mL). The mixture was extracted with ether (2×300 mL) and the combined ether layers were dried (MgSO4), filtered and concentrated. The resulting black oil was purified by flash chromatography on silica gel eluting with a solvent gradient from 10% to 25% ethyl acetate in hexanes to provide 12.3 g of the title compound (81%) as a light yellow liquid. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.81 (s, 3H) 7.01 (dd, J=9.01, 3.13 Hz, 1H) 7.18-7.21 (m, 1H) 7.23 (t, J=3.13 Hz, 2H) 7.47 (d, J=9.19 Hz, 1H); MS (ESI) m/z 241.9 (M+H)+.

후처리

  1. temperaturecooled to ambient temperature
  2. extractionThe mixture was extracted with ether (2×300 mL)
  3. dry with materialthe combined ether layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting black oil was purified by flash chromatography on silica gel eluting with a solvent gradient from 10% to 25% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-0030590b6e25478f8b085bb6eb5edfce
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748627B2

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