Ethyl Acetate → HCID 18357133, compound

HRID 427447Notes

Reaction equation

HRID 427447 reaction equation
[C:1]([C:8]1[NH:9][CH:10]=[CH:11][N:12]=1)([C:3]1[NH:4][CH:5]=[CH:6]N=1)=O.[Br:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([S:24](O)=O)[CH:18]=[CH:17]2.[C:27](OCC)(=O)[CH3:28]>CN(C)C=O>[N:4]1[CH:3]=[CH:1][C:8]([N:9]2[CH2:10][CH2:11][N:12]([S:24][C:19]3[CH:18]=[CH:17][C:16]4[C:21](=[CH:22][CH:23]=[C:14]([Br:13])[CH:15]=4)[CH:20]=3)[CH2:28][CH2:27]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 17915795HCID 17915795, compound

Product 1

HCID 18357133HCID 18357133, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Carbonyl diimidazole (324 mg) was added to a solution of 6-bromonaphthalene-2-sulphinic acid (658 mg) in dimethylformamide (10 ml). After stirring at ambient temperature for one hour N-4-(4-pyridyl)piperazine (326 mg) was added as a solid in one portion and stirring continued at ambient temperature overnight. The reaction mixture was poured into ethyl acetate (100 ml), washed with water (3×25 ml), brine (25 ml), dried (MgSO4) and evaporated to give a yellow oil which was purified by chromatography on silica gel (Mega Bond Elut column) using an increasing concentration of methanol in dichloromethane (up to 5% methanol) as eluant to give an oil which on trituration with diethyl ether gave a white solid 1-(4-pyridyl)-4-(6-bromonaphtalene-2-sulphenyl)piperazine (170 mg), m.p. 200-202° C.; microanalysis, found: C, 54.9; H, 4.4; N, 10.1; C19H18BrN3OS requires: C, 54.9; H, 4.3; N, 10.1; NMR: 2.9-3.0(m,2H); 3.1-3.3(m,2H); 3.35-3.5(m,4H); 6.8(dd,2H); 7.7-7.8(m,2H); 8.1-8.2(m,4H); 8.3(s,1H); 8.35(d,1H); MS: m/z 416 (MH)+.

Workup

  1. additionwas added as a solid in one portion
  2. washwashed with water (3×25 ml), brine (25 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a yellow oil which
  6. customwas purified by chromatography on silica gel (Mega Bond Elut column)
  7. customto give an oil which on trituration with diethyl ether

Sources & evidence

ORD record
ord-3183913771ee4bb2b1f0e898d434522d
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

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