Allyl bromide → HCID 20507740, compound

HRID 128079Notes

Reaction equation

HRID 128079 reaction equation
[N:1]1([C:7]2[N:8]=[C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=[C:10]3[N:11]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[CH:24]=[CH2:25]>CS(C)=O.[Cl-].[Na+].O>[CH2:25]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[N:11]=[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]3[N:8]=2)[CH2:2][CH2:3]1)[CH:24]=[CH2:23]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 13036368HCID 13036368, compound

Product 1

HCID 20507740HCID 20507740, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 2-(1-piperazinyl)cycloheptimidazole (3.15 g, described in Example 2) and potassium carbonate (1.14 g) in dimethyl sulfoxide (10 ml) was stirred for 15 min and a solution of 2-propenyl bromide (1.18 g) in dimethyl sulfoxide was added. The reaction mixture was stirred for 2.5 hr and diluted with brine. The solution was extracted with ethyl acetate and the organic extract was dried and evaporated to give the title compound (1.8 g): mp 108°-111° C.; ir(CHCl3) 1600, 1565 and 1520 cm-1 ; uv max (MeOH) 263(ε29,965), 237(ε25,490) and 362 nm (ε21,620) and nmr(CDCl3)δ 2.6(4H,s), 3.0(2H,d), 4.05(4H,t), 5.15(2H,m), 5.75(1H,m) and 7.65(5H,m).

Workup

  1. stirringThe reaction mixture was stirred for 2.5 hr
  2. extractionThe solution was extracted with ethyl acetate
  3. extractionthe organic extract
  4. customwas dried
  5. customevaporated

Sources & evidence

ORD record
ord-6ac9863b3c254022abed5e08ed686052
Source dataset
uspto-grants-1981_03
Patent number
US04258188

Reaction notes

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