Hydrochloric Acid → HCID 178424894, compound

HRID 893742Notes

Reaction equation

HRID 893742 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[NH4+].[CH3:7][C:8]1([CH3:30])[CH2:17][CH2:16][C:15]([CH3:19])([CH3:18])[C:14]2[CH:13]=[C:12]([C:20]#[C:21][C:22]3[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=3)[CH:11]=[CH:10][C:9]1=2.Cl>CN(C)C=O.O>[CH3:7][C:8]1([CH3:30])[CH2:17][CH2:16][C:15]([CH3:18])([CH3:19])[C:14]2[CH:13]=[C:12]([C:20]#[C:21][C:22]3[CH:29]=[CH:28][C:25]([C:26]4[NH:27][N:3]=[N:2][N:1]=4)=[CH:24][CH:23]=3)[CH:11]=[CH:10][C:9]1=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 136048264-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzonitrile

Product 1

HCID 178424894HCID 178424894, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2.15 g (0.033 mole) of sodium azide, 1.77 g (0.033 mole) of ammonium chloride and 9.2 g (0.03 mole) of 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-ethynyl]-benzonitrile in 30 ml of absolute dimethylformamide were stirred for 12 hours at 120° C. The cooled reaction mixture was then poured onto 0.5 liter of water and acidified with a little hydrochloric acid. The crystals which had separated out were filtered off under suction, washed on the filter several times with water and then with methanol, sucked dry while hot, and dried in a stream of nitrogen. 9.0 g (84%) of the title compound of melting point 227°-228° C. were obtained.

Workup

  1. customThe cooled reaction mixture
  2. customThe crystals which had separated out
  3. filtrationwere filtered off under suction
  4. washwashed on the filter several times with water
  5. dry with materialwith methanol, sucked dry while hot, and
  6. customdried in a stream of nitrogen

Sources & evidence

ORD record
ord-f5e4565baba44e96b3d3e114e74917c1
Source dataset
uspto-grants-1992_06
Patent number
US05126371

Reaction notes

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