Water → HCID 21459524, compound

HRID 1941003Notes

Reaction equation

HRID 1941003 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° to 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-03b3545f4dbd4f4686ad1fd98ba9b4c4
Source dataset
uspto-grants-1997_12
Patent number
US05702681

Reaction notes

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