2-Methylthiazole → 5-(2-Methoxy-4-nitro-phenyl)-2-methyl-thiazole

HRID 2076126ノート

反応式

HRID 2076126 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].C([O-])(=O)C.[K+].[CH3:18][C:19]1[S:20][CH:21]=[CH:22][N:23]=1>CN(C)C(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[C:21]1[S:20][C:19]([CH3:18])=[N:23][CH:22]=1

参加物

6

反応物 3

HCID 771292-MethylthiazoleHCID 1012932-Bromo-5-nitroanisoleHCID 517044Potassium Acetate

生成物 1

HCID 670963525-(2-Methoxy-4-nitro-phenyl)-2-methyl-thiazole収率 42.6%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 31374Dimethylacetamide溶媒

実験手順

In a microwave vial a mixture of 2-bromo-5-nitroanisole (800 mg, 3.38 mmol), potassium acetate (503 mg, 5.07 mmol) and tetrakis(triphenylphosphine)-palladium(0) (197 mg, 0.17 mmol) in N,N-dimethylacetamide (12 mL) was flushed with argon while 2-methylthiazole (1.71 g, 16.9 mmol) was added. The tube was sealed and the mixture was irradiated 2 times for 30 minutes in a microwave oven at 160° C. The red-brown mixture was partitioned between ethyl acetate and water. The water layer was re-extracted with ethyl acetate. The combined organic phases were washed three times with water, once with brine, dried with magnesium sulfate and evaporated to dryness. Column chromatography (70 g silica, heptane/ethyl acetate 7:3 v/v) afforded the title compound (360 mg, 42%) as a yellow solid. MS ISP (m/e): 251.1 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.15 (s, 1H), 7.90 (dd, 1H), 7.84 (s, 1H), 7.72 (d, 1H), 4.05 (s, 3H), 2.76 (s, 3H). mp 114-117° C.

後処理

  1. additionwas added
  2. customThe tube was sealed
  3. customthe mixture was irradiated 2 times for 30 minutes in a microwave oven at 160° C
  4. customThe red-brown mixture was partitioned between ethyl acetate and water
  5. extractionThe water layer was re-extracted with ethyl acetate
  6. washThe combined organic phases were washed three times with water
  7. dry with materialonce with brine, dried with magnesium sulfate
  8. customevaporated to dryness

出典と根拠

ORDレコード
ord-7a1eab6efdcc440786e15bbe5a6c7e56
出典データセット
uspto-grants-2011_04
特許番号
US07923450B2

反応ノート

読み込み中…