Hydrochloric Acid → HCID 13069856, compound

HRID 1902842Notes

Reaction equation

HRID 1902842 reaction equation
[Na].[NH:2]1[CH:6]=[N:5][CH:4]=[N:3]1.[OH-].[Na+].[C:9]([C:11]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[Cl:29])([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:12]Br)#[N:10].Cl>CS(C)=O.CCOCC.O>[C:9]([C:11]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[Cl:29])([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:12][N:2]1[CH:6]=[N:5][CH:4]=[N:3]1)#[N:10]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 92571H-1,2,4-Triazole2×HCID 14798Sodium HydroxideHCID 5360545SodiumHCID 53836477HCID 53836477, compound

Product 1

HCID 13069856HCID 13069856, compoundYield 28.2%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To 7.0 g (0.07697 mole) of the sodium salt of 1H-1,2,4-triazole, generated from 5.3 g; (0.07697 mole) of 1H-1,2,4-triazole and 3.1 g (0.759 mole) of NaOH, in 50 ml of DMSO, is added 30.0 g (0.0767 mole) of 2-cyano-2-(2,4-dichlorophenyl) decyl bromide (prepared by the usual route); and the reaction is stirred at 130° for 20 hours. The mixture is then cooled and mixed with 200 ml of water. The organic material which separates is extracted 2×100 ml of ether, and the extract is washed 2×50 ml of water, dried over anhydrous magnesium sulfate and concentrated to give 24.0 g (82.5%) of the crude product. This material is dissolved in ether, and it is treated with hydrogen chloride gas until it is acidic to litmus. The solid which precipitates is separated by filtration to give 9.0 g (28.2%) of the hydrochloric salt, mp 125°-31°. To 6.7 g (0.0161 mole) of the hydrochloride salt in 200 ml of water is stirred. The organic soluble material is extracted 2×200 ml of ether, and the extract is washed 2×50 ml of water, dried over anhydrous magnesium sulfate, and concentrated to give 4.9 g (80.2%) of the oil product.

Workup

  1. customprepared by the usual route)
  2. temperatureThe mixture is then cooled
  3. extractionThe organic material which separates is extracted 2×100 ml of ether
  4. washthe extract is washed 2×50 ml of water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto give 24.0 g (82.5%) of the crude product
  8. customThe solid which precipitates
  9. customis separated by filtration

Sources & evidence

ORD record
ord-75edb4343c97460796a5ca722b8121fb
Source dataset
uspto-grants-1982_12
Patent number
US04366165

Reaction notes

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