5-(2-Methoxy-4-nitro-phenyl)-2-methyl-thiazole → 3-Methoxy-4-(2-methyl-thiazol-5-yl)-phenylamine

HRID 1855504ノート

反応式

HRID 1855504 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:12]1[S:16][C:15]([CH3:17])=[N:14][CH:13]=1>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[C:12]1[S:16][C:15]([CH3:17])=[N:14][CH:13]=1

参加物

3

反応物 1

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

生成物 1

HCID 670959033-Methoxy-4-(2-methyl-thiazol-5-yl)-phenylamine収率 91.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A suspension of 5-(2-methoxy-4-nitro-phenyl)-2-methyl-thiazole (330 mg, 1.32 mmol) and anhydrous stannous chloride (1.28 g, 6.6 mmol) in ethanol (21 mL) was stirred at reflux for one hour. The yellow solution was evaporated and the residue dissolved in ethyl acetate. This solution was washed twice with 2N aqueous sodium hydroxide solution, with brine, dried with magnesium sulfate and evaporated to dryness to afford the title compound (266 mg, 91%) as an orange solid. MS ISP (m/e): 221.2 [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.81 (s, 1H), 7.33 (d, 1H), 6.31 (m, 2H), 3.87 (s, 3H), 3.83 (m, 2H), 2.69 (s, 3H). Mp 125-129° C.

後処理

  1. temperatureat reflux for one hour
  2. customThe yellow solution was evaporated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washThis solution was washed twice with 2N aqueous sodium hydroxide solution, with brine
  5. dry with materialdried with magnesium sulfate
  6. customevaporated to dryness

出典と根拠

ORDレコード
ord-594a650122d548a3b36daccf2611566b
出典データセット
uspto-grants-2015_02
特許番号
US08962834B2

反応ノート

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