Sodium Chloride → HCID 23302846, compound

HRID 1953248Notes

Reaction equation

HRID 1953248 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)=[O:7])=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22].[K].[CH3:25]C(C)([O-])C.CI.[Cl-].[Na+]>CS(C)=O>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([N:8]([CH3:25])[C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)=[O:7])=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 765824HCID 765824, compoundHCID 50987170Potassium tertbutoxide

Product 1

HCID 23302846HCID 23302846, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3.2 g (0.01 mol) of 4-chloro-3-nitro-N-(naphthalen-1-yl)-benzamide and 1.1 g (0.01 mol) of potassium-tert.-butoxide are dissolved in 50 ml dimethylsulphoxide and stirred for 30 minutes at ambient temperature. Then 1 ml methyl iodide is added thereto and the mixture is stirred for a further 3 hours at ambient temperature. The solution is poured onto saturated sodium chloride solution and extracted with ethyl acetate. The combined organic extracts are dried over sodium sulphate and concentrated by evaporation. The residue is chromatographed on silica gel and eluted with methylene chloride.

Workup

  1. stirringthe mixture is stirred for a further 3 hours at ambient temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts are dried over sodium sulphate
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on silica gel
  6. washeluted with methylene chloride

Sources & evidence

ORD record
ord-59b730bfc2fb47fd8b873e84d2806513
Source dataset
uspto-grants-2000_09
Patent number
US06114532

Reaction notes

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