Thionyl Chloride → 3-(chloromethyl)-5-nitro-1H-pyrazole

HRID 70353Notes

Reaction equation

HRID 70353 reaction equation
[N+:1]([C:4]1[NH:8][N:7]=[C:6]([CH2:9]O)[CH:5]=1)([O-:3])=[O:2].O=S(Cl)[Cl:13]>C(Cl)Cl>[Cl:13][CH2:9][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[NH:8][N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 135636628(3-nitro-1H-pyrazol-5-yl)methanol

Product 1

HCID 1361755593-(chloromethyl)-5-nitro-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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).

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-ccfe0f6b48e7448983a6e0991534499a
Source dataset
uspto-grants-2014_09
Patent number
US08822530B2

Reaction notes

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