Hydrochloric Acid → HCID 86600617, compound

HRID 859857Notes

Reaction equation

HRID 859857 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.Cl.[N+:13]([O-])([O-])=O.[Na+].[Cl:18][C:19]1[N:24]=[CH:23][C:22]([CH2:25][NH:26][C:27](=[O:31])[CH2:28][C:29]#[N:30])=[CH:21][CH:20]=1.C([O-])(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O.C(OCC)(=O)C.C(O)C.C(O)(=O)C>[Cl:18][C:19]1[N:24]=[CH:23][C:22]([CH2:25][NH:26][C:27](=[O:31])[C:28]([C:29]#[N:30])=[N:13][NH:7][C:6]2[CH:8]=[CH:9][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:4][CH:5]=2)=[CH:21][CH:20]=1

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 99644-(Trifluoromethyl)anilineHCID 10340Sodium CarbonateHCID 24268Sodium NitrateHCID 517045Sodium AcetateHCID 12993667HCID 12993667, compound

Product 1

HCID 86600617HCID 86600617, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

4-Trifluoromethyl aniline (0.97 g, 6.0 mmol) was gradually added to acetic acid (3.5 ml), water (1.7 ml) and concentrated hydrochloric acid (1.7 ml) and dissolved, and cooled to 5° C. A solution of sodium nitrate (0.5 g, 7.2 mmol) in water (2 ml) was gradually added thereto at a temperature of 10° C. or less. The resulting solution was gradually added to a mixture of N-(6-chloro-3-pyridylmethyl)-2-cyanoacetic acid amide (1.3 g, 6.0 mmol), sodium acetate (1.23 g, 15.0 mmol), ethanol (30 ml) and 1N aqueous solution of sodium carbonate (40 ml). After stirring at room temperature for 5 hours, water and ethyl acetate were added thereto and subjected to extraction. The organic phase was washed with a saturated brine, and dried on anhydrous sodium sulfate. The residue obtained by filtering and concentrating was purified with a silica gel chromatography to obtain N-(6-chloro-3-pyridylmethyl)-2-cyano-2-(4-trifluoromethylphenyl hydrazono) acetic acid amide (Compound No. 184) (0.12 g, 0.30 mmol, 5%) (Compound No. 185) (1.15 g, 3.00 mmol, 50%). Geometrical isomerism (E/Z) was not determined.

Workup

  1. dissolutiondissolved
  2. customat a temperature of 10° C. or less
  3. extractionsubjected to extraction
  4. washThe organic phase was washed with a saturated brine
  5. dry with materialdried on anhydrous sodium sulfate
  6. customThe residue obtained
  7. filtrationby filtering
  8. concentrationconcentrating
  9. customwas purified with a silica gel chromatography

Sources & evidence

ORD record
ord-f9e21dbaf2c34d1389d639a5298c929a
Source dataset
uspto-grants-2006_12
Patent number
US07153815B2

Reaction notes

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