Hydrochloric Acid → HCID 178466122, compound

HRID 1683800Notes

Reaction equation

HRID 1683800 reaction equation
[Cl-].[NH4+].[N-:3]=[N+:4]=[N-:5].[Na+].[CH2:7]([O:9][C:10]1[CH:11]=[C:12]([C:19]2[S:20][CH:21]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]#[N:31])[N:25]=3)[N:23]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH3:18])[CH3:8].Cl>CN(C)C=O>[CH2:7]([O:9][C:10]1[CH:11]=[C:12]([C:19]2[S:20][CH:21]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]4[NH:31][N:5]=[N:4][N:3]=4)[N:25]=3)[N:23]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH3:18])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 19041048HCID 19041048, compound

Product 1

HCID 178466122HCID 178466122, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

280 mg of ammonium chloride and 380 mg of sodium azide were added to a solution of 1.5 g of 2-(3,4-diethoxyphenyl)-4-(6-cyano-2-pyridyl)thiazole dissolved in 30 ml of dimethylformamide. The mixture was stirred at 120° C. for 9 hours. To the reaction mixture was added diluted hydrochloric acid to make the mixture acidic, followed by extraction three times with 150 ml of ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate. The solvent was removed by distillation. The residue was recrystallized from ethanol-ethyl acetate to obtain 1.19 g of 2-(3,4-diethoxyphenyl)-4-[6-(1,2,3,4-tetrazol-5-yl)-2-pyridyl]thiazole.

Workup

  1. extractionfollowed by extraction three times with 150 ml of ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  3. customThe solvent was removed by distillation
  4. customThe residue was recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-c627f87ba29642deb1a80b2e0740ad60
Source dataset
uspto-grants-1997_06
Patent number
US05639770

Reaction notes

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