Thionyl Chloride → Ethyl 5-(chloromethyl)-1,3-dimethyl-1H-pyrazole-4-carboxylate

HRID 64564Notes

Reaction equation

HRID 64564 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:14])=[N:8][N:9]([CH3:13])[C:10]=1[CH2:11]O)=[O:5])[CH3:2].S(Cl)([Cl:17])=O>ClCCl>[Cl:17][CH2:11][C:10]1[N:9]([CH3:13])[N:8]=[C:7]([CH3:14])[C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 125200244-Ethoxycarbonyl-5-(1-hydroxymethyl)-1,3-dimethylpyrazole

Product 1

HCID 13729351Ethyl 5-(chloromethyl)-1,3-dimethyl-1H-pyrazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This material was combined with the product of a second reaction (5.0 g of 4-ethoxycarbonyl-5-(1-hydroxymethyl)-1,3-dimethylpyrazole and 1.93 ml thionyl chloride), dissolved in dichloromethane, washed with brine, dried (MgSO4) and concentrated to give 10.7 g of a solid, mp. 81°-83° C.

Workup

  1. washwashed with brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5e7d334209e543728745a51b4443d951
Source dataset
uspto-grants-1986_09
Patent number
US04609397

Reaction notes

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