Chlorosuccinimide → HCID 18980127, compound

HRID 2392691Notes

Reaction equation

HRID 2392691 reaction equation
[CH3:1][N:2]([CH3:34])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[N:31]=[C:30]([CH3:32])[O:29][N:28]=4)=[CH:23][C:22]=3[CH3:33])=[CH:17][CH:16]=2)=[O:14])[CH:9]=[CH:10][CH:11]=1.[Cl:35]N1C(=O)CCC1=O>ClCCl>[CH3:1][N:2]([CH3:34])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:35])=[C:8]([NH:12][C:13]([C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[N:31]=[C:30]([CH3:32])[O:29][N:28]=4)=[CH:23][C:22]=3[CH3:33])=[CH:19][CH:20]=2)=[O:14])[CH:7]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 18980145HCID 18980145, compound

Product 1

HCID 18980127HCID 18980127, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-[3-(2dimethylaminoethoxy)phenyl]-2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxamide (E13) (200 mg) in dichloromethane (10 ml) was treated with N-chlorosuccinimide (64 mg) and the mixture stirred at room temperature overnight. The reaction mixture was evaporated under reduced pressure, and the residue triturated with diethyl ether and the precipitated succinimide was removed by filtration. The filtrate was evaporated under reduced pressure and flash column chromatographed on silica gel, eluting with dichloromethane, then chloroform and methanol to give the title compound. (77 mg, 36%). Mp 101°-2° C.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customthe residue triturated with diethyl ether
  3. customthe precipitated succinimide was removed by filtration
  4. customThe filtrate was evaporated under reduced pressure and flash column
  5. customchromatographed on silica gel
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-2b04a62f8713415b9bf266e13646d6e6
Source dataset
uspto-grants-1998_09
Patent number
US05801170

Reaction notes

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