Trifluoroacetic acid → HCID 14500608, compound

HRID 1761598Notes

Reaction equation

HRID 1761598 reaction equation
[CH2:1]([N:4]1[C:8]([CH2:9][CH2:10][CH3:11])=[CH:7][CH:6]=[C:5]1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=1)[CH2:2][CH3:3].[O-:20][C:21]#[N:22].[Na+].FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1>[CH2:1]([N:4]1[C:8]([CH2:9][CH2:10][CH3:11])=[CH:7][CH:6]=[C:5]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][CH3:3]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 517096Sodium CyanateHCID 14500607HCID 14500607, compound

Product 1

HCID 14500608HCID 14500608, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A stirred solution of 2 g (7.7 mmol) of 1,5-dipropyl-2-(3'-aminobenzyl)pyrrole in 200 ml of benzene was treated with 1 g (15.3 mmol) of sodium cyanate followed by the dropwise addition, over a 11/2 hour period, of a solution of 1.5 ml (19 mmol) of trifluoroacetic acid in 100 ml of benzene. The reaction mixture was stirred at room temperature for 1 more hour, poured into 300 ml of saturated aqueous sodium carbonate solution and extracted with ethyl acetate (3×300 ml). The combined extracts were washed with water (2×300 ml), dried and evaporated in vacuo. The residue was purified by column chromatography on 100 g of silica gel, using hexane-ethyl acetate (55:45) as eluant, thus obtaining 1.85 g (83%) of the title compound, 1,5-dipropyl-2-(3'-ureidobenzyl)pyrrole, which was recrystallized from acetone-hexane. M.P. 123°-126° C.

Workup

  1. additionfollowed by the dropwise addition, over a 11/2 hour period
  2. extractionextracted with ethyl acetate (3×300 ml)
  3. washThe combined extracts were washed with water (2×300 ml)
  4. customdried
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on 100 g of silica gel

Sources & evidence

ORD record
ord-d96e69dd11e0453a9c32623a15087ea0
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

Loading…