Sodium Carbonate → HCID 11609103, 화합물

HRID 1820142노트

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HRID 1820142 반응식
[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]

참가 물질

6

반응물 2

HCID 10340Sodium CarbonateHCID 68707090HCID 68707090, 화합물

생성물 1

HCID 11609103HCID 11609103, 화합물수율 100%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-0f6ef7153c1942eda14bb36e162c66f5
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601870B2

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