Thionyl Chloride → Ethyl 4-(chloromethyl)-1,2,5-trimethylpyrrole-3-carboxylate

HRID 1764699Notes

Reaction equation

HRID 1764699 reaction equation
O[CH2:2][C:3]1[C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([CH3:10])[N:6]([CH3:9])[C:7]=1[CH3:8].S(Cl)([Cl:18])=O>C1C=CC=CC=1>[Cl:18][CH2:2][C:3]1[C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([CH3:10])[N:6]([CH3:9])[C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13051083Ethyl 4-(hydroxymethyl)-1,2,5-trimethylpyrrole-3-carboxylate

Product 1

HCID 20528801Ethyl 4-(chloromethyl)-1,2,5-trimethylpyrrole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1.0 g of ethyl 4-(hydroxymethyl)-1,2,5-trimethyl-pyrrole-3-carboxylate is dissolved in 15 ml of benzene and 0.6 g of thionyl chloride is added dropwise and after total addition the reaction mixture is stirred for 3.5 hours at ambient temperature. The benzene is removed in vacuo leaving the gray solid, ethyl 4-(chloromethyl)-1,2,5-trimethylpyrrole-3-carboxylate.

Workup

  1. additionafter total addition the reaction mixture
  2. customThe benzene is removed in vacuo

Sources & evidence

ORD record
ord-b1dbee1a853e4c73b228567091e90d02
Source dataset
uspto-grants-1978_09
Patent number
US04117152

Reaction notes

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