Trifluoroacetic acid → HCID 14500618, compound

HRID 1761577Notes

Reaction equation

HRID 1761577 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([N:11]1[C:15]([CH2:16][CH3:17])=[CH:14][CH:13]=[C:12]1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=1)[CH2:9][CH3:10].[O-:26][C:27]#[N:28].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.CO>[CH2:8]([N:11]1[C:15]([CH2:16][CH3:17])=[CH:14][CH:13]=[C:12]1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][C:27]([NH2:28])=[O:26])[CH:20]=1)[CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 517096Sodium CyanateHCID 14500617HCID 14500617, compound

Product 1

HCID 14500618HCID 14500618, compoundYield 74.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3.5 ml (39 mmol) of trifluoroacetic acid in 200 ml of methylene chloride was added dropwise, over a 2 hour period and under nitrogen atmosphere, to a stirred suspension of 4.8 g (19 mmol) of 1-propyl-2-(3'-aminobenzyl)-5-ethylpyrrole and 2.58 g (39 mmol) of sodium cyanate in 400 ml of anhydrous methylene chloride and 90 ml of methanol. The reaction mixture was stirred at room temperature for 18 additional hours, 2 g (18 mmol) of sodium carbonate were added and the solvent evaporated under reduced pressure. The residue was purified by column chromatography on 300 g of silica gel, using hexane-acetone (1:1) as eluant, obtaining 4.04 g (72%) of the title compound, 1-propyl-2-(3'-ureidobenzyl)-5-ethylpyrrole, which was recrystallized from ether-hexane. M.P. 116°-118° C.

Workup

  1. additionwere 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-cad5c4b62ac3450181f464d5dac5608c
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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