Water → 4-Chloro-5-(2-methoxy-5-nitro-phenyl)-1-methyl-1H-pyrazole

HRID 540530노트

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HRID 540530 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[C:12]1[N:16]([CH3:17])[N:15]=[CH:14][CH:13]=1.[Cl:18]N1C(=O)CCC1=O.O>CN(C=O)C>[Cl:18][C:13]1[CH:14]=[N:15][N:16]([CH3:17])[C:12]=1[C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

참가 물질

5

반응물 3

HCID 962WaterHCID 31398Chlorosuccinimide2회HCID 231395315-(2-Methoxy-5-nitrophenyl)-1-methyl-1H-pyrazole

생성물 1

HCID 231395374-Chloro-5-(2-methoxy-5-nitro-phenyl)-1-methyl-1H-pyrazole수율 89%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

5-(2-Methoxy-5-nitro-phenyl)-1-methyl-1H-pyrazole (2.37 g, 10.17 mmol) was dissolved in DMF (100 mL). The solution was then heated to 80° C. N-Chlorosuccinimide (1.49 g, 11.1 mmol) was added at 80° C. under Argon gas. After two hours of continuous stirring, the reaction was checked by TLC and LCMS, and found to be incomplete. An additional aliquot of NCS (0.5 g, 3.7 mmol) was added, bringing the reaction to completion after 1.5 hours. While stirring, a portion of water (200 mL) was added to force the product to precipitate out of solution. After the precipitation was complete, the flask containing the solid was cooled in an ice water bath for 10 minutes. The solid was then filtered under vacuum and rinsed with water, yielding 2.4 g (89%) of 4-chloro-5-(2-methoxy-5-nitro-phenyl)-1-methyl-1H-pyrazole. This material was used in the next step without purification. LCMS m/z (%)=267 (M+H, 100). 1H NMR (400 MHz, CDCl3) δ: 8.41 (dd, J1=8 Hz, J2=4 Hz, 1H), 8.22 (d, J=4 Hz, 1H), 7.53 (s, 1H), 7.14 (d, J=12 Hz, 1H), 3.97 (s, 3H), 3.72 (s, 3H).

후처리

  1. customthe reaction to completion after 1.5 hours
  2. customto precipitate out of solution
  3. customAfter the precipitation
  4. additionthe flask containing the solid
  5. temperaturewas cooled in an ice water bath for 10 minutes
  6. filtrationThe solid was then filtered under vacuum
  7. washrinsed with water

출처 및 근거

ORD 기록
ord-860b039eeb2644e481a86ccc349f0e89
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871797B2

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