Hydrochloric Acid → HCID 71255681, compound

HRID 1508331Notes

Reaction equation

HRID 1508331 reaction equation
[Cl:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=2[F:14])[N:5]=[N:4][C:3]=1[C:15]([O:17]CC)=[O:16].Cl.N(OCCC(C)C)=O>CCO.CCOC(C)=O>[Cl:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=2[F:14])[N:5]=[N:4][C:3]=1[C:15]([OH:17])=[O:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 71255453HCID 71255453, compound

Product 1

HCID 71255681HCID 71255681, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 5-chloro-1-(3-chloro-2-fluorophenyl)-1H-1,2,3-triazole-4-carboxylate: (Can. J. Chem., 37:118-119 (1959)). To a solution of Intermediate 27A (1.1 g, 3.86 mmol) in EtOH (30 mL) at 0° C. was passed HCl gas until all of the solid dissolved. To the solution was added isoamyl nitrite (0.520 mL, 3.86 mmol) in one portion and the resulting solution was kept at 0-5° C. for 48 h. The reaction mixture was diluted in EtOAc and washed with aq NaHCO3 and brine. The organic layer was concentrated and purified by reverse phase HPLC to yield the desired product. MS(ESI) m/z: 304.0 (M+H)+.

Workup

  1. customat 0° C.
  2. dissolutiondissolved
  3. washwashed with aq NaHCO3 and brine
  4. concentrationThe organic layer was concentrated
  5. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-787fcdbec91543ac967ba8a1e72211dc
Source dataset
uspto-grants-2015_12
Patent number
US09221818B2

Reaction notes

Loading…