Water → HCID 21459524, compound

HRID 1590578Notes

Reaction equation

HRID 1590578 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[C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19].O>O1CCCC1>[Br:10][C:4]1[N:3]([C:18]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:19])[C:2]([Br:1])=[C:6]([C:7]#[N:8])[C:5]=1[Br:9]

Participants

6

Reactant 4

HCID 962WaterHCID 15891Phenyl chloroformateHCID 10471741HCID 10471741, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21459524HCID 21459524, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7.0 g of 2,4,5-tribromopyrrole-3-carbonitrile and 2.9 g of potassium t-butoxide in tetrahydrofuran is treated with 13.8 g of phenyl chloroformate, heated at reflux temperature for 12 hours, cooled, poured into water and filtered. The solid filter cake is washed with water and dried in vacuo to afford the title compound. A sample is recrystallized from a mixture of ethyl acetate and methylcyclohexane to give colorless crystals, mp 128°-129° C.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 12 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. filtrationThe solid filter cake
  6. washis washed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-fbc71d1a26b4478fad86a2932c783b01
Source dataset
uspto-grants-1993_04
Patent number
US05204332

Reaction notes

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