Acetic Acid → HCID 18537078, 화합물

HRID 2298628노트

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HRID 2298628 반응식
[C:1]([C:5]1[CH:9]=[C:8](C(Cl)=O)[N:7]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C[Si](C=[N+]=[N-])(C)C.[BrH:27].[C:28]([OH:31])(=O)[CH3:29]>C(#N)C>[C:1]([C:5]1[CH:9]=[C:8]([C:28](=[O:31])[CH2:29][Br:27])[N:7]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 167693TrimethylsilyldiazomethaneHCID 27993221-benzyl-3-tert-butyl-1H-pyrazole-5-carbonyl chloride

생성물 1

HCID 18537078HCID 18537078, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 1 g (3.6 mmol) of 3-(tert-butyl)-1-benzylpyrazole-5-carbonyl chloride (Maybridge, Cornwall, UK) was dissolved in dry acetonitrile (4 mL) and 4.5 mL (9 mmol) of 2 M trimethylsilyldiazomethane in hexanes (Aldrich, Milwaukee, Wis., USA) was added. After stirring 1 h 20 min at room temperature, the mixture was cooled on an ice bath for 5 min. To this, 30% hydrogen bromide in acetic acid (2 mL, 10 mmol) was added dropwise over 15 min. This was stirred an additional 15 minutes on an ice bath. Filtration of the precipitated solid and evaporation of the solvents gave 1-[3-(tert-butyl)-1-benzylpyrazol-5-yl]-2-bromoethan-1-one (1.47 g, quantitive yield) as an orange solid. 1H-NMR (DMSO-d6; 300 MHz) δ7.33-7.06 (m, 5H), 7.08 (s, 1H), 5.64 (s, 2H), 4.57 (s, 2H), 1.28 (s, 9H). Mass spectrum (MALDI-TOF, CHCA matrix, m/z): Calcd. for C16H19N2OBr, 335.1 and 337.1 (M+H), found 335.6 and 337.6.

후처리

  1. temperaturethe mixture was cooled on an ice bath for 5 min
  2. stirringThis was stirred an additional 15 minutes on an ice bath
  3. filtrationFiltration of the precipitated solid and evaporation of the solvents

출처 및 근거

ORD 기록
ord-65807bceb76d4aefa509376736f0a9a5
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06492403B1

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