Trifluoroacetic acid → HCID 14500646, compound

HRID 1761594Notes

Reaction equation

HRID 1761594 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([N:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=1)[CH2:9][CH2:10][CH3:11].[O-:25][C:26]#[N:27].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1>[CH2:8]([N:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:26]([NH2:27])=[O:25])[CH:19]=1)[CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 517096Sodium CyanateHCID 14500645HCID 14500645, compound

Product 1

HCID 14500646HCID 14500646, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 3.5 ml (45 mmol) of trifluoroacetic acid in 25 ml of benzene was added dropwise to a suspension of 5 g (21 mmol) of 1-butyl-2-(3'-aminobenzyl)pyrrole and 2.85 g (43 mmol) of sodium cyanate in 250 ml of benzene. The reaction mixture was stirred at room temperature for 1 hour further and then poured into 600 ml of saturated sodium carbonate solution. The organic phase was separated and the aqueous phase extracted with ethyl acetate (3×300 ml). The combined extracts were washed with water (2×250 ml), dried and evaporated under reduced pressure. The residue was purified by column chromatography on 300 g of silica gel, using hexane-ethyl acetate (30:70) as eluant, thus obtaining 3.82 g (65%) of the title compound, 1-butyl-2-(3'-ureidobenzyl)pyrrole, which was recrystallized from acetone-hexane.

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous phase extracted with ethyl acetate (3×300 ml)
  3. washThe combined extracts were washed with water (2×250 ml)
  4. customdried
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on 300 g of silica gel

Sources & evidence

ORD record
ord-71435fafbd8f4488b1fe15becfa41a34
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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