4-Butylaniline → HCID 59151596, compound

HRID 1260846Notes

Reaction equation

HRID 1260846 reaction equation
[C:1]([CH:3]([CH:7]1[C:11]([Cl:12])=[C:10](Cl)C(=O)O1)[C:4]([NH2:6])=[O:5])#[N:2].[CH2:15]([C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1)[CH2:16][CH2:17][CH3:18].C(N(CC)CC)C>C(O)C>[CH2:15]([C:19]1[CH:20]=[CH:21][C:22]([N:23]2[CH:10]=[C:11]([Cl:12])[CH:7]=[C:3]([C:4]([NH2:6])=[O:5])[C:1]2=[NH:2])=[CH:24][CH:25]=1)[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 76944-ButylanilineHCID 8471TriethylamineHCID 5417922-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamide

Product 1

HCID 59151596HCID 59151596, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (0.5 g) in ethanol (10 ml) was added 4-butylaniline (0.95 g) (Table 1-2, amine 69), and the mixture was stirred at room temperature for 17 hr. Triethylamine (0.65 g) was added, and the mixture was further stirred at room temperature for 5 hr. The reaction mixture was concentrated and dissolved in a mixture of dimethyl sulfoxide (5 ml)-water (5 ml), and the mixture was stirred at 80° C. for 3 hr. The reaction mixture was concentrated, the residue was purified by preparative HPLC, and the obtained fraction was treated with PL-HCO3 MP (200 mg cartridge, Polymer Laboratories) to give the title compound (0.15 g). HPLC purity 94%. MS m/z 304 (M+H+).

Workup

  1. stirringthe mixture was further stirred at room temperature for 5 hr
  2. concentrationThe reaction mixture was concentrated
  3. dissolutiondissolved in a mixture of dimethyl sulfoxide (5 ml)-water (5 ml)
  4. stirringthe mixture was stirred at 80° C. for 3 hr
  5. concentrationThe reaction mixture was concentrated
  6. customthe residue was purified by preparative HPLC
  7. additionthe obtained fraction was treated with PL-HCO3 MP (200 mg cartridge, Polymer Laboratories)

Sources & evidence

ORD record
ord-03a20ccb661a41bb92646e194c44d58e
Source dataset
uspto-grants-2013_06
Patent number
US08470859B2

Reaction notes

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