Water → HCID 21847708, compound

HRID 1289459Notes

Reaction equation

HRID 1289459 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:13](C)[C:14]#[N:15])[C:8](=[O:17])[C:7](=[O:18])[NH:6]2.[N-]=[N+:22]=[N-:23].[Na+].[Cl-].[NH4+].O.[CH3:28][N:29](C)C=O>>[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][N:15]1[N:23]=[N:22][CH:28]=[N:29]1)[C:8](=[O:17])[C:7](=[O:18])[NH:6]2

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 54299062HCID 54299062, compound

Product 1

HCID 21847708HCID 21847708, compoundYield 37.8%

Conditions

Temperature
120 °C

Procedure

345 mg (1.2 mmol) of 3-[(6-trifluoromethylquinoxaline-2,3-dion-1-yl)propionitrile is heated together with 407 mg (6.3 mmol) of sodium azide and 333 mg (6.3 mmol) of ammonium chloride in 13 ml of dimethylformamide for 3 hours to 120° C. bath temperature. After adding once more 203 mg (3.2 mmol) of sodium azide and 160 mg (3.1 mmol) of ammonium chloride, it is heated for 5 hours more to 120° C. bath temperature. After dilution with water and adjusting the pH to 2, it is extracted with ethyl acetate. During the shaking out with saturated common salt solution, the desired compound is precipitated from the organic phase. By concentration by evaporation of the organic phase and absorptive precipitation in ethyl acetate, another fraction is obtained. Altogether, 150 mg (37.8% of theory) of 2-[(6 trifluoromethylquinoxaline-2,3-dion-1-yl)ethyl]-tetrazole of melting point 279.8° C. is obtained.

Workup

  1. extractionis extracted with ethyl acetate
  2. customDuring the shaking out with saturated common salt solution, the desired compound is precipitated from the organic phase
  3. concentrationBy concentration
  4. customby evaporation of the organic phase and absorptive precipitation in ethyl acetate
  5. customanother fraction is obtained

Sources & evidence

ORD record
ord-47afc01b2e294f44abe3e6968044d6c5
Source dataset
uspto-grants-1998_05
Patent number
US05750525

Reaction notes

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