Hydrochloric Acid → HCID 14013848, compound

HRID 1763154Notes

Reaction equation

HRID 1763154 reaction equation
C(ON=O)(C)(C)C.[F:8][CH:9]([F:31])[C:10]1[N:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[C:13]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:12](N)[C:11]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27].N#N.[ClH:34]>CC#N.[Cu](Cl)Cl>[F:8][CH:9]([F:31])[C:10]1[N:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[C:13]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:12]([Cl:34])[C:11]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 10906Tert-Butyl nitriteHCID 14013845HCID 14013845, compound

Product 1

HCID 14013848HCID 14013848, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent2×

Procedure

To a mechanically stirred mixture of 11.52 g of (0.087 mol) of copper (II) chloride, and 11.18 g (0.108 mol) of t-butylnitrite in 350 ml of CH3CN, was added a solution of 25.00 g (0.070 mol) of product of Example 100 in 25 ml of CH3CN in such a rate that a slow evolution of N2 was observed. After 18 hours the mixture was poured into 3.7% HCl, and extracted with diethyl ether. The ether phase was washed with H2O, and dried (MgSO4). This was concentrated in vacuo to 24.03 g of a yellow oil. The crude product was purified by HPLC in 5% ethyl acetate/cyclohexane affording 13.2 g (50%) of product as a yellow solid; mp 35°-40° C.

Workup

  1. extractionextracted with diethyl ether
  2. washThe ether phase was washed with H2O
  3. dry with materialdried (MgSO4)
  4. concentrationThis was concentrated in vacuo to 24.03 g of a yellow oil
  5. customThe crude product was purified by HPLC in 5% ethyl acetate/cyclohexane affording 13.2 g (50%) of product as a yellow solid

Sources & evidence

ORD record
ord-dff58e7c481e43bfb040f3de1c8a5b90
Source dataset
uspto-grants-1989_05
Patent number
US04835279

Reaction notes

Loading…