Diethyl Ether → HCID 21080267, compound

HRID 346669Notes

Reaction equation

HRID 346669 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[Br:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([S:24]([C:27]1[CH:37]=[C:31]3[C:32]([O:34][C:35](=[O:36])[C:30]3=[CH:29][CH:28]=1)=[O:33])(=[O:26])=[O:25])[CH:18]=[CH:17]2.C(OCC)C>CN(C=O)C>[Br:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([S:24]([C:27]1[CH:28]=[CH:29][C:30]([C:35]([N:10]3[CH2:9][CH2:8][N:7]([C:4]4[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=4)[CH2:12][CH2:11]3)=[O:36])=[C:31]([CH:37]=1)[C:32]([OH:34])=[O:33])(=[O:26])=[O:25])[CH:18]=[CH:17]2.[Br:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([S:24]([C:27]1[CH:28]=[CH:29][C:30]([C:35]([OH:36])=[O:34])=[C:31]([C:32]([N:10]3[CH2:9][CH2:8][N:7]([C:4]4[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=4)[CH2:12][CH2:11]3)=[O:33])[CH:37]=1)(=[O:26])=[O:25])[CH:18]=[CH:17]2

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 705171-(4-Pyridyl)piperazineHCID 54229121HCID 54229121, compound

Product 2

HCID 21080267HCID 21080267, compoundHCID 21080275HCID 21080275, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(4-Pyridyl)piperazine (0.163 g) was added, in one portion, to a stirred solution of 5-(6-bromonaphth-2-ylsulphonyl)phthalic anhydride (0.417 g.) in DMF (10 ml.) and the mixture was stirred at ambient temperature for 1 hour. Diethyl ether (40 ml.) was added and the mixture was stirred rapidly. The resultant white, amorphous precipitate was recovered by filtration. There was thus obtained a 1:1 mixture (0.474 g., 81%) of: 5-(6-bromonaphth-2-ylsulphonyl)-2-[4-(4-pyridyl)piperazin-1-ylcarbonyl]benzoic acid and 4-(6-bromonaphth-2-ylsulphonyl)-2-[4-(4-pyridyl)piperazin-1-ylcarbonyl]benzoic acid; the mixture giving the following characterising data;

Workup

  1. stirringthe mixture was stirred rapidly
  2. filtrationThe resultant white, amorphous precipitate was recovered by filtration

Sources & evidence

ORD record
ord-e74d4dbfc51b4c1da1a263bd2a55af1a
Source dataset
uspto-grants-2007_02
Patent number
US07173025B1

Reaction notes

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