4-Methyl-5-(2-hydroxyethyl)thiazole → HCID 69219983、化合物

HRID 272697

反応式

HRID 272697 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 69219983HCID 69219983、化合物収率 86.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-409df72e33cf45d8a976a3b4eefceee5
出典データセット
uspto-grants-2008_11
特許番号
US07456169B2

関連ノート

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