Chlorosuccinimide → HCID 23139479, compound

HRID 919495Notes

Reaction equation

C1C(=O)N([Cl:8])C(=O)C1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1[C:20]1[N:24]([CH3:25])[N:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1>CN(C=O)C>[Cl:8][C:21]1[C:22]([C:26]([F:29])([F:27])[F:28])=[N:23][N:24]([CH3:25])[C:20]=1[C:12]1[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:11]=1[O:10][CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

NCS (0.05 g, 0.37 mmol, 1.1 eq.) dissolved in DMF (⅔ mL) was added drop wise to a stirred solution of 5-(2-methoxy-5-nitro-phenyl)-1-methyl-3-trifluoromethyl-1H-pyrazole, see Example 1.99 (0.1 g, 0.33 mmol) in DMF (1⅓ mL) at 0° C. The reaction mixture was stirred 0° C. and TLC indicated no product. An additional equivalent of NCS was added and the reaction mixture was stirred at 80° C. overnight which resulted in completion of the reaction. The DMF was removed under vacuum and the crude mixture was diluted with EtOAc (50 mL) and washed with brine (3×10 mL). The EtOAc phase was dried over anhydrous MgSO4, filtered and evaporated to give the partially purified product 4-chloro-5-(2-methoxy-5-nitro-phenyl)-1-methyl-3-trifluoromethyl-1H-pyrazole (0.13 g) as a light yellow solid: LCMS m/z (%)=336 (M+H35Cl, 100), 382 (M+H37Cl, 33). 1H NMR (400 MHz, CDCl3) δ: 8.37 (dd, J=8.0, 4.0 Hz, 1H), 8.16 (d, J=4.0 Hz 1H), 7.09 (d, J=8.0 Hz, 1H), 3.92 (s, 3H), 3.69 (s, 3H).

Workup

customat 0° C
stirringthe reaction mixture was stirred at 80° C. overnight which
customresulted in completion of the reaction
customThe DMF was removed under vacuum
additionthe crude mixture was diluted with EtOAc (50 mL)
washwashed with brine (3×10 mL)
dry with materialThe EtOAc phase was dried over anhydrous MgSO4
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-07d4462b6aeb4bebaf2a0c78f55feaef
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273035B2

Reaction notes

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