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

HRID 67178Notes

Reaction equation

HRID 67178 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-trimethylpyrrole-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-570b696b1ab54383ac12278f407844c5
Source dataset
uspto-grants-1982_08
Patent number
US04345087

Reaction notes

Loading…