Benzyl Bromide → HCID 21947667, compound

HRID 2214438Notes

Reaction equation

HRID 2214438 reaction equation
[CH3:1][S:2][C:3]1[NH:4][C:5]2[C:10](=[O:11])[N:9]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[N:8]=[CH:7][C:6]=2[N:23]=1.[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH2:24]([N:4]1[C:5]2[C:10](=[O:11])[N:9]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[N:8]=[CH:7][C:6]=2[N:23]=[C:3]1[S:2][CH3:1])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178503361HCID 178503361, compound

Product 1

HCID 21947667HCID 21947667, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1.0 g (3.10 mmol) of 2-methylsulphanyl-5-(naphthalen-1-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one in 15 ml of dimethylformamide was combined with 547 mg (3.20 mmol) of benzylbromide and then with 442 mg (3.20 mmol) of potassium carbonate and stirred overnight at ambient temperature. Then it was diluted with approx. 40 ml of water and extracted three times with 15 ml of ethyl acetate. The organic extracts were washed with water, dried over sodium sulphate and evaporated down. The crude product thus obtained was purified by column chromatography (silica gel; eluant:petroleum ether with 10–20% ethyl acetate).

Workup

  1. extractionextracted three times with 15 ml of ethyl acetate
  2. washThe organic extracts were washed with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated down

Sources & evidence

ORD record
ord-be9c3030169d49be95b89256452ab8ee
Source dataset
uspto-grants-2006_09
Patent number
US07109192B2

Reaction notes

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