Hydrochloric Acid → HCID 178526616, compound

HRID 1721380Notes

Reaction equation

HRID 1721380 reaction equation
Cl.C(N(CC)CC)C.[N-:9]=[N+:10]=[N-:11].[Na+].[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]#[N:24])=[CH:18][CH:17]=1)([O-:15])=[O:14].Cl>CN1CCCC1=O>[NH:9]1[C:23]([CH2:22][C:19]2[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:21][CH:20]=2)=[N:24][N:11]=[N:10]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 68386p-Nitrophenylacetonitrile

Product 1

HCID 178526616HCID 178526616, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

Triethylamine hydrochloride (41.25 g, 0.3 mol) and sodium azide (39 g, 0.6 mol) were added to a solution of 4-nitrophenylacetonitrile (32.4 g, 0.2 mmol) in anhydrous N-methylpyrrolidin-2-one (500 ml) and the mixture heated at 150° C. for 4h. The solution was cooled to room temperature and poured into 2N HCl (2 l) whereupon a solid crystallised out. The product was filtered, washed with water (500 ml) and hexane and dried in vacuo (37.4 g); δ (250 MHz, CDCl3) 4.34 (2H, s, CH2), 7.42 (2H, d, J=8.7 Hz, Ar--H), 8.12 (2H, d, J=8.7 Hz, Ar--H).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customcrystallised out
  3. filtrationThe product was filtered
  4. washwashed with water (500 ml) and hexane
  5. customdried in vacuo (37.4 g)

Sources & evidence

ORD record
ord-14d1d71996ff4e149327d4be35609b60
Source dataset
uspto-grants-1996_04
Patent number
US05510362

Reaction notes

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