1,1'-Carbonyldiimidazole → HCID 9805660, compound

HRID 346661Notes

Reaction equation

C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl: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:35]=[CH:34][C:30]([C:31](O)=[O:32])=[CH:29][CH:28]=1)(=[O:26])=[O:25])[CH:18]=[CH:17]2.[N:36]1[CH:41]=[CH:40][C:39]([N:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)=[CH:38][CH:37]=1>CN(C=O)C>[Cl: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:31]([N:45]3[CH2:46][CH2:47][N:42]([C:39]4[CH:40]=[CH:41][N:36]=[CH:37][CH:38]=4)[CH2:43][CH2:44]3)=[O:32])=[CH:34][CH:35]=1)(=[O:26])=[O:25])[CH:18]=[CH:17]2

Participants

Conditions

Temperature: 0 °C

Procedure

1,1′-Carbonyldiimidazole (0.15 g) was added to a stirred solution of 4-(6-chloronaphth-2-ylsulphonyl)benzoic acid (0.29 g) in DMF (10 ml) which had been cooled to 0° C. and the mixture was stirred at 0° C. for 30 minutes. N-(4-Pyridyl)piperazine (0.164 g) was added, the cooling bath was removed and the mixture was stirred at ambient temperature for 16 hours. The solvent was removed by evaporation and the residue was partitioned between ethyl acetate and water. The ethyl acetate extract was washed with water and with brine, dried (MgSO4) and evaporated. The residue was triturated under diethyl ether to give 1-[4-(6-chloronaphth-2-ylsulphonyl)benzoyl]-4-(4-pyridyl)piperazine (0.085 g), m.p. 267-269° C.;

Workup

customthe cooling bath was removed
stirringthe mixture was stirred at ambient temperature for 16 hours
customThe solvent was removed by evaporation
customthe residue was partitioned between ethyl acetate and water
extractionThe ethyl acetate extract
washwas washed with water and with brine
dry with materialdried (MgSO4)
customevaporated
customThe residue was triturated under diethyl ether

Sources & evidence

ORD record: ord-9c8fc16626af49a48bf54c01c603bf57
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173025B1

Reaction notes

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