Sodium Carbonate → HCID 11609103、化合物

HRID 1820142ノート

反応式

HRID 1820142 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([NH:11][C:12](=[O:18])[CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[C:4]([CH3:19])[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C(O)(=O)C.[Zn]>[NH2:8][C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[C:4]([CH3:19])[C:5]=1[NH:11][C:12](=[O:18])[CH2:13][C:14]([CH3:16])([CH3:15])[CH3:17]

参加物

6

反応物 2

HCID 10340Sodium CarbonateHCID 68707090HCID 68707090、化合物

生成物 1

HCID 11609103HCID 11609103、化合物収率 100%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

Zinc dust (16 g) was added in portions over 2 hours to N-(4-bromo-2-methyl-6-nitro-phenyl)-3,3-dimethyl-butyramide (2.74 g) in tetrahydrofuran (50 mL) and acetic acid (12 mL) cooled to 0° C., and then stirred 30 minutes at 25° C. The reaction mixture was poured into a suspension of sodium carbonate (16 g) in tetrahydrofuran and filtered through silica (50 g), which was washed with ethyl acetate (100 mL). The organic phase was concentrated in vacuo to furnish 2.47 g (100% yield) of the title compound as a pale red solid. LC-MS (m/z) 300 (MH+); tR=2.54, (UV, ELSD) 96%, 99%. 1H NMR (500 MHz, DMSO-d6): 1.04 (s, 9H), 2.05 (s, 3H), 2.21 (s, 2H), 4.94 (s, 2H), 6.59 (d, 1H), 6.74 (d, 1H), 8.85 (s, 1H).

後処理

  1. filtrationfiltered through silica (50 g), which
  2. washwas washed with ethyl acetate (100 mL)
  3. concentrationThe organic phase was concentrated in vacuo

出典と根拠

ORDレコード
ord-0f6ef7153c1942eda14bb36e162c66f5
出典データセット
uspto-grants-2009_10
特許番号
US07601870B2

反応ノート

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