Chlorosuccinimide → 4-chloro-1-isopropyl-5-(2-methoxy-5-nitro-phenyl)-1H-pyrazole

HRID 919476Notes

Reaction equation

HRID 919476 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=2[O:18][CH3:19])=[CH:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].C1C(=O)N([Cl:27])C(=O)C1>CN(C=O)C>[Cl:27][C:7]1[CH:6]=[N:5][N:4]([CH:1]([CH3:3])[CH3:2])[C:8]=1[C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[O:18][CH3:19]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 231394531-isopropyl-5-(2-methoxy-5-nitro-phenyl)-1H-pyrazole

Product 1

HCID 231394924-chloro-1-isopropyl-5-(2-methoxy-5-nitro-phenyl)-1H-pyrazoleYield 97.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred, ice-cooled solution of 1-isopropyl-5-(2-methoxy-5-nitro-phenyl)-1H-pyrazole from Example 1.81, Step C (1.0 g, 3.83 mmol) in DMF (10 mL) was added NCS (0.56 g, 4.22 mmol) over a period of 10 minutes. The reaction mixture was warmed to ambient temperature and stirred at 55° C. for 6 h. The reaction mixture was cooled and poured into an ice-water mixture with vigorous stirring to form a white solid, which was filtered and washed with cold water until free of DMF. The solid was dried in vacuo to yield 4-chloro-1-isopropyl-5-(2-methoxy-5-nitro-phenyl)-1H-pyrazole (1.1 g, 97%). LCMS m/z (%)=296 M+H+, (35Cl, 100), 298 (37Cl, 28.5). 1H NMR (400 MHz, CDCl3) δ: 8.4 (dd, J1=9.09 Hz, J2=2.78 Hz, 1H), 8.19 (d, J=2.8 Hz), 7.6 (s, 1H), 7.14 (d, J=9.18 Hz, 1H), 4.10 (m, 1H), 3.94 (s, 3H), 1.49 (d, J=6.62 Hz, 3H), 1.36 (d, J=6.62 Hz, 3H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. stirringwith vigorous stirring
  3. customto form a white solid, which
  4. filtrationwas filtered
  5. washwashed with cold water until free of DMF
  6. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-347f0e534c4f4848b4dda289b50327f4
Source dataset
uspto-grants-2016_03
Patent number
US09273035B2

Reaction notes

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