Urea → HCID 53861673, compound

HRID 582563Notes

Reaction equation

HRID 582563 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=2)=[O:13])[CH:8]=[CH:9][CH:10]=1)#[N:4].Br[CH2:25][CH2:26][CH2:27][CH2:28]Br.N[C:31](N)=O.C(O[CH2:38][CH3:39])(=O)C>CN(C)C=O.CCCCCC>[C:3]([C:5]1[CH:6]=[C:7]([N:11]([CH:25]2[CH2:39][CH2:38][CH2:31][CH2:28][CH2:27][CH2:26]2)[C:12]([NH:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]#[N:23])=[CH:20][CH:21]=2)=[O:13])[CH:8]=[CH:9][CH:10]=1)#[N:4]

Participants

8

Reactant 5

HCID 1176UreaHCID 80561,4-DibromobutaneHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 18630729HCID 18630729, compound

Product 1

HCID 53861673HCID 53861673, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of sodium hydride (0.29 g of a 60 % suspension in mineral oil, 7.28 mmol) in dimethylformamide (45 ml) at ambient temperature was added a dimethylformamide solution (5 ml) of N-(3-cyanophenyl)-N'-((4-cyanophenyl)methyl)urea (0.67 g, 2.43 mmol). This mixture was stirred for 30 min before 1,4-dibromobutane (1.05 g, 4.85 mmol) in dimethylformamide (10 ml) was added over 20 min. The reaction was then heated at 70° C. for 1 h, after which analysis by thin layer chromatography (1:2 hexane:ethyl acetate) demonstrated that all of the starting urea had been consumed. The cooled reaction mixture was poured into ice water and extracted with ethyl acetate (3×). The extract was washed with 1N HCl and brine, then dried (Na2SO4) and evaporated. The crude product was purified by flash chromatography on a column of silica gel with 1:1 hexane:ethyl acetate as the eluent. There was obtained 0.47 g of pure N-(3-cyanophenyl)-N'-((4-cyanophenyl)methyl)cycloheptyl-urea; LRMS: (M+H)+ m/z 331.

Workup

  1. additionwas added over 20 min
  2. customhad been consumed
  3. customThe cooled reaction mixture
  4. extractionextracted with ethyl acetate (3×)
  5. washThe extract was washed with 1N HCl and brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe crude product was purified by flash chromatography on a column of silica gel with 1:1 hexane

Sources & evidence

ORD record
ord-0ea719d6033e4d318fb19addbbdf25a4
Source dataset
uspto-grants-1999_07
Patent number
US05925635

Reaction notes

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