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

HRID 2419759Notes

Reaction equation

HRID 2419759 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-f2cfa432401545078ae9868516eb8eb8
Source dataset
uspto-grants-1978_08
Patent number
US04107321

Reaction notes

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