Ethyl cyanoacetate → HCID 71255659, compound

HRID 1508330Notes

Reaction equation

HRID 1508330 reaction equation
[NH2:1][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].CC[O-].[Na+].C(CC(OCC)=O)#N.N(C1C=CC=C(Cl)C=1F)=[N+]=[N-]>CCO.O>[NH2:1][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

7

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 2723922Sodium ethoxideHCID 43154621HCID 43154621, compoundHCID 71255710HCID 71255710, compound

Product 1

HCID 71255659HCID 71255659, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 5-amino-1-(3-chloro-2-fluorophenyl)-1H-1,2,3-triazole-4-carboxylate: (PCT International Application No. 2006/047516 (2006)) To a solution of NaOEt (4.99 g, 15.39 mmol) in EtOH (10 mL) at 0° C. was added ethyl 2-cyanoacetate (1.501 ml, 14.11 mmol). The reaction was stirred at 0° C. for 10 min and added 1-azido-3-chloro-2-fluorobenzene (2.2 g, 12.82 mmol). The reaction was allowed to slowly warm up to rt and stirred for 14 h. The mixture was treated with water (3 mL) and extracted with EtOAc (3×30 mL). The combined extracts were concentrated and purified by silica gel chromatography to yield the desired product (2.1 g, 58%). MS(ESI) m/z: 285.1 (M+H)+.

Workup

  1. temperatureto slowly warm up to rt
  2. stirringstirred for 14 h
  3. extractionextracted with EtOAc (3×30 mL)
  4. concentrationThe combined extracts were concentrated
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-2b22ea3772c64825942e9482858ffafa
Source dataset
uspto-grants-2015_12
Patent number
US09221818B2

Reaction notes

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