Sodium Sulfite → HCID 23316360, compound

HRID 1982391Notes

Reaction equation

HRID 1982391 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][CH:17]=[CH:16][C:5]=1[CH2:6][N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]([O:14][CH3:15])=[O:13])([O-:3])=[O:2].[Cl:20]N1C(=O)CCC1=O.S([O-])([O-])=O.[Na+].[Na+]>O1CCCC1>[N+:1]([C:4]1[CH:19]=[CH:18][CH:17]=[CH:16][C:5]=1[CH2:6][N:7]1[C:11]([Cl:20])=[CH:10][CH:9]=[C:8]1[C:12]([O:14][CH3:15])=[O:13])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 31398ChlorosuccinimideHCID 13649487HCID 13649487, compound

Product 1

HCID 23316360HCID 23316360, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.5 g of methyl 1-(2-nitrobenzyl)pyrrole-2-carboxylate in 50 mL of dry tetrahydrofuran is added 1.54 g of N-chlorosuccinimide. The reaction is allowed to stir at room temperature for 48 hours. To the reaction mixture is added sodium sulfite, the reaction is stirred for an additional 1 hour, filtered and evaporated to dryness. The residue is extracted into 200 mL of ether, the extract is dried over anhydrous magnesium sulfate and evaporated to dryness to yield methyl 1-(2-nitrobenzyl)-5-chloropyrrole-2-carboxylate which is used in the next step without further purification.

Workup

  1. stirringthe reaction is stirred for an additional 1 hour
  2. filtrationfiltered
  3. customevaporated to dryness
  4. extractionThe residue is extracted into 200 mL of ether
  5. dry with materialthe extract is dried over anhydrous magnesium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-28a2810b531a429bb87f7df9c86c7df7
Source dataset
uspto-grants-1986_06
Patent number
US04596799

Reaction notes

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