Potassium Carbonate → 5-chloro-2-(((5-nitro-1H-pyrazol-3-yl)methyl)thio)aniline

HRID 70354

Reaction equation

HRID 70354 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[SH:9].Cl[CH2:11][C:12]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[NH:14][N:13]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([S:9][CH2:11][C:12]2[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[NH:14][N:13]=2)=[C:2]([CH:7]=1)[NH2:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 120002-Amino-4-chlorobenzenethiolHCID 1361755593-(chloromethyl)-5-nitro-1H-pyrazole

Product 1

HCID 1363723895-chloro-2-(((5-nitro-1H-pyrazol-3-yl)methyl)thio)anilineYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(5-Nitro-1H-pyrazol-3-yl)methanol (524 mg, 3.66 mmol) was first treated with SOCl2 (3 ml) in CH2Cl2 (5 ml) at 35° C. for 2 hrs. The solvent was removed to get a crude 3-(chloromethyl)-5-nitro-1H-pyrazole. Then following General Procedure A, the title compound (515 mg, 49%) was prepared from 2-amino-4-chlorobenzenethiol (161 mg, 1.01 mmol), crude 3-(chloromethyl)-5-nitro-1H-pyrazole, K2CO3 (468 mg, 3.39 mmol) in DMF (3 ml).

Sources & evidence

ORD record
ord-a10a1cf7815243f2b4c580629e4fc303
Source dataset
uspto-grants-2014_09
Patent number
US08822530B2

Linked notes

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