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

HRID 404896

反応式

HRID 404896 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 694346862-Chloro-4-methoxyphenoxy-1,3-thiazole収率 81%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-0030590b6e25478f8b085bb6eb5edfce
出典データセット
uspto-grants-2014_06
特許番号
US08748627B2

関連ノート

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