4-Chlorobenzoyl chloride → HCID 21459525, compound

HRID 1492064Notes

Reaction equation

HRID 1492064 reaction equation
[Br:1][C:2]1[NH:3][C:4]([Br:10])=[C:5]([Br:9])[C:6]=1[C:7]#[N:8].CC(C)([O-])C.[K+].[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1>O1CCCC1.O.C(OCC)(=O)C>[Br:1][C:2]1[N:3]([C:22](=[O:23])[C:21]2[CH:25]=[CH:26][C:18]([Cl:17])=[CH:19][CH:20]=2)[C:4]([Br:10])=[C:5]([Br:9])[C:6]=1[C:7]#[N:8]

Participants

7

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 10471741HCID 10471741, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21459525HCID 21459525, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2,4,5-tribromopyrrole-3-carbonitrile (5.0 g, 0.015 mol) and potassium T-butoxide (2.0 g, 0.018 mol) in dry tetrahydrofuran is stirred for 10 minutes at room temperature, treated dropwise with a solution of p-chlorobenzoyl chloride (3.25 g, 0.018 mol) in tetrahydrofuran, heated at reflux temperature for 3 hours, cooled and diluted with a mixture of water and ethyl acetate. The organic phase is separated, washed with brine, dried over Na2SO4 and concentrated in vacuo to afford a tan solid residue. Recrystallization from benzene gives the title compound as a cream colored solid, 2.9 g (41.4%), mp 154°-157° C.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 3 hours
  3. temperaturecooled
  4. customThe organic phase is separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto afford a tan solid residue
  9. customRecrystallization from benzene

Sources & evidence

ORD record
ord-1a499e83a53c4dfa86ed354c35fceae1
Source dataset
uspto-grants-1994_12
Patent number
US05371239

Reaction notes

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