1,2-Dibromoethane → HCID 66615017, compound

HRID 717628Notes

Reaction equation

HRID 717628 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[NH:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Br[CH2:27][CH2:28]Br>CN(C=O)C>[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH2:28][CH2:27][N:17]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:16]2=[O:25])=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 78391,2-DibromoethaneHCID 66615004Ethyl 3-(3-(4-octylphenyl)ureido)propanoate

Product 1

HCID 66615017HCID 66615017, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the product of Example 11, Step A (0.05 g; 0.143 mmol) in anhydrous DMF (2 ml) 60% NaH in mineral oil (0.014 g; 0.344 mmol) was added at room temperature. After stirring for 1 h, to it 1,2-dibromoethane (0.172 ml; 0.2 mmol) was added. This was stirred at ˜50° C. for 1 h under N2, cooled to room and solvents were removed in vacuo. The residue was diluted to 15 ml with Et2O, washed with H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane/EtOAc 9.5:0.5) to give the title compound (0.02 g; 37%) as a colourless solid. 1H-NMR (CDCl3) 7.4 (d, 2H, J=8.5 Hz); 7.1 (d, 2H, J=8.5 Hz); 4.13 (q, 2H, J=7.1 Hz); 3.76 (m, 2H); 3.57 (t, 2H, J=6.7 Hz); 3.5 (m, 2H); 2.6 (t, 2H, J=6.7 Hz); 2.53 (t, 2H, J=7.9 Hz); 1.55 (m, 2H); 1.24 (m, 13H); 0.85 (t, 3H, J=6.9 Hz).

Workup

  1. additionwas added
  2. temperaturecooled to room and solvents
  3. customwere removed in vacuo
  4. additionThe residue was diluted to 15 ml with Et2O
  5. washwashed with H2O, brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customThe filtrate was evaporated under reduced pressure
  9. customthe residue was purified by FCC (SiO2, hexane/EtOAc 9.5:0.5)

Sources & evidence

ORD record
ord-6ac86822e0fb43a4bdb78e3b446254aa
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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