Hydrochloric Acid → HCID 86649639, compound

HRID 1913489Notes

Reaction equation

HRID 1913489 reaction equation
N(OCCC(C)C)=O.N[C:10]1[N:15]=[C:14]([S:16][CH2:17][C:18]2[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=2)[C:21]([OH:23])=[O:22])[C:13]([C:27]#[N:28])=[C:12]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][OH:38])=[CH:31][CH:30]=2)[C:11]=1[C:39]#[N:40].[ClH:41]>C(#N)C.[Cu](Cl)Cl>[Cl:41][C:10]1[N:15]=[C:14]([S:16][CH2:17][C:18]2[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=2)[C:21]([OH:23])=[O:22])[C:13]([C:27]#[N:28])=[C:12]([C:29]2[CH:30]=[CH:31][C:32]([O:35][CH2:36][CH2:37][OH:38])=[CH:33][CH:34]=2)[C:11]=1[C:39]#[N:40]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 66672075HCID 66672075, compound

Product 1

HCID 86649639HCID 86649639, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

262 mg (2.24 mmol) of isopentyl nitrite and 301 mg (2.24 mmol) of copper(II) chloride were initially charged in 10.4 ml of acetonitrile. 500 mg (1.12 mmol) of the compound from Example 5A were added, and the mixture was then stirred at 60° C. for 4 h. After cooling to RT, 2.2 ml of 1N hydrochloric acid were added. The aqueous phase was extracted three times with in each case 30 ml of ethyl acetate. The combined organic phases were washed once with saturated aqueous sodium bicarbonate solution, twice with water and once with saturated aqueous sodium chloride solution and dried over sodium sulfate. After removal of the solvent, the product was used without further purification for the subsequent reaction.

Workup

  1. temperatureAfter cooling to RT
  2. extractionThe aqueous phase was extracted three times with in each case 30 ml of ethyl acetate
  3. washThe combined organic phases were washed once with saturated aqueous sodium bicarbonate solution, twice with water and once with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customAfter removal of the solvent
  6. customthe product was used without further purification for the subsequent reaction

Sources & evidence

ORD record
ord-1bc9e8715d0144288c611198a9665072
Source dataset
uspto-grants-2013_12
Patent number
US08609686B2

Reaction notes

Loading…