Ammonium Chloride → HCID 69250022, compound

HRID 2370917Notes

Reaction equation

HRID 2370917 reaction equation
[CH:1]1([N:6]2[CH:10]=[C:9]([CH2:11][C:12]([O:14][CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[O:13])[N:8]=[CH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si](C)(C)N[Si](C)(C)C.[Li].C([C:32]([O:34][CH3:35])=[O:33])#N.[NH4+].[Cl-]>O1CCCC1>[CH:1]1([N:6]2[CH:10]=[C:9]([CH:11]([C:32]([O:34][CH3:35])=[O:33])[C:12]([O:14][CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19]3)=[O:13])[N:8]=[CH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 28660Carbonocyanidic acid, methyl esterHCID 57426343Lithium bis(trimethylsilyl)amideHCID 86612812HCID 86612812, compound

Product 1

HCID 69250022HCID 69250022, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Cyclopentyl (1-cyclopentyl-1H-imidazol-4-yl)acetate (2.00 g; 7.60 mmol) was dissolved in tetrahydrofuran (THF; 45 ml). The reaction solution was cooled to 0° C. and then lithium hexamethyldisilazane (20% in THF; 6.33 ml; 7.60 mmol) was added dropwise. The mixture was stirred at 0° C. for a further hour. Then methyl cyanoformate (0.66 ml; 8.36 mmol) was added. The mixture was stirred at 0° C. for 10 min and then at RT for 7 h. The reaction solution was then added to saturated NH4Cl solution. It was extracted with EA, and the organic phase was washed with H2O and dried over Na2SO4. The solvent was removed under reduced pressure. Purification of the crude product by column chromatography (120 g of silica gel; EtOAc/n-heptane—2/1) resulted in 0.46 g of cyclopentyl methyl 2-(1-cyclopentyl-1H-imidazol-4-yl)malonate.

Workup

  1. stirringThe mixture was stirred at 0° C. for 10 min
  2. extractionIt was extracted with EA
  3. washthe organic phase was washed with H2O
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customPurification of the crude product by column chromatography (120 g of silica gel; EtOAc/n-heptane—2/1)
  7. customresulted in 0.46 g of cyclopentyl methyl 2-(1-cyclopentyl-1H-imidazol-4-yl)malonate

Sources & evidence

ORD record
ord-8434ce1940774f79a3b6af26f5cf3c23
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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