Trifluoroacetic acid → HCID 14500626, compound

HRID 1761583Notes

Reaction equation

HRID 1761583 reaction equation
[CH2:1]([N:5]1[C:9]([CH2:10][CH3:11])=[CH:8][CH:7]=[C:6]1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=1)[CH2:2][CH2:3][CH3:4].[O-:20][C:21]#[N:22].[Na+].FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.CO>[CH2:1]([N:5]1[C:9]([CH2:10][CH3:11])=[CH:8][CH:7]=[C:6]1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:21]([NH2:22])=[O:20])[CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 517096Sodium CyanateHCID 14500625HCID 14500625, compound

Product 1

HCID 14500626HCID 14500626, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 3.1 g (12 mmol) of 1-butyl-2-(3'-aminobenzyl)-5-ethylpyrrole in 250 ml of dry methylene chloride and 50 ml of anhydrous methanol was treated, at room temperature and under nitrogen atmosphere, with 1.7 g (26 mmol) of sodium cyanate, followed by the dropwise addition, over a 2 hour period, of 2.3 ml (29 mmol) of trifluoroacetic acid in 100 ml of methylene chloride. The reaction mixture was stirred at room temperature for 18 additional hours, 2 g (18 mmol) of sodium carbonate were then added and the solvent evaporated under reduced pressure. The residue was purified by column chromatography on 300 g of silica gel, using methylene chloride-methanol (97:3) as eluant, thus obtaining 3.4 g (93%) of the title compound, 1-butyl-2-(3'-ureidobenzyl)-5-ethylpyrrole, which was recrystallized from ether-hexane.

Workup

  1. additionwere then added
  2. customthe solvent evaporated under reduced pressure
  3. customThe residue was purified by column chromatography on 300 g of silica gel

Sources & evidence

ORD record
ord-50617d764346464ab5e5993be440bad8
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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