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

HRID 866771Notes

Reaction equation

HRID 866771 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-839cfba5fb3c47e1b8c16987980d5f13
Source dataset
uspto-grants-1978_07
Patent number
US04101559

Reaction notes

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