Water → HCID 15222095, compound

HRID 274819Notes

Reaction equation

HRID 274819 reaction equation
[CH2:1]([C:4]1[NH:5][C:6]([C:13]([O:15][CH3:16])=[O:14])=[C:7]([C:9]([O:11][CH3:12])=[O:10])[N:8]=1)[CH2:2][CH3:3].[Br:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:12][O:11][C:9]([C:7]1[N:8]=[C:4]([CH2:1][CH2:2][CH3:3])[N:5]([CH2:22][C:21]2[CH:24]=[CH:25][C:18]([Br:17])=[CH:19][CH:20]=2)[C:6]=1[C:13]([O:15][CH3:16])=[O:14])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 15222105Dimethyl 2-propyl-1H-imidazole-4,5-dicarboxylate

Product 1

HCID 15222095HCID 15222095, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 40.0 g (0.177 mole) of 2-propyl-4,5-bis(methoxycarbonyl)-imidazole and 44.6 g (0.178 mole) of 4-bromobenzyl bromide in 350 mL of DMF was stirred in the presence of 37.5 g (0.271 mole) of K2CO3 overnight at room temperature. The reaction mixture was then poured into 1200 mL of water and extracted with 3×300 mL of ether. The combined ether extracts were washed with 8×1000 mL of water and once with brine, then dried over MgSO4. The solvent was removed under reduced pressure to yield 61.8 g (88%) of the title compound as a solid. 1H NMR (300 MHz, CDCl3): δ 0.94 (t, J=7.6 Hz, 3H); 1.73 (m, 2H); 2.63 (t, J=7.9 Hz, 2H); 3.81 (s, 3H); 3.93 (s, 3H); 5.37 (s, 2H); 6.86 (d, J=8.8 Hz, 2H); 7.45 (d, J=8.8 Hz, 2H). MS [DCI (NH3)]: m/z 395/397 (M+H, 1 Br).

Workup

  1. extractionextracted with 3×300 mL of ether
  2. washThe combined ether extracts were washed with 8×1000 mL of water and once with brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5e1add3b0c09484ab94ad77f0ac99d4d
Source dataset
uspto-grants-1995_02
Patent number
US05389635

Reaction notes

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