Hydrochloric Acid → HCID 58142729, compound

HRID 1640335Notes

Reaction equation

HRID 1640335 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][NH:5][NH2:6].Cl.Cl[CH:13](OCC)[C:14]([O:16][CH2:17][CH3:18])=[O:15].[OH-].[Na+]>O.O1CCOCC1>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][NH:5]/[N:6]=[CH:13]/[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2724873Ethyl 2-chloro-2-ethoxyacetateHCID 10374537(2-Fluorobenzyl)hydrazine

Product 1

HCID 58142729HCID 58142729, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

(2-Fluorobenzyl)hydrazine (1.00 g, 7.14 mmol) is suspended in water (3 ml), and the mixture is brought to pH 4 with 4N hydrochloric acid. It is then cooled in an ice bath, and a solution of ethyl chloro(ethoxy)acetate (1.37 g, 8.21 mmol) in dioxane (10 ml) is added. The mixture is stirred at RT for 1 h, then made weakly alkaline (pH 8) with 1N sodium hydroxide solution and extracted with ethyl acetate. The organic phase is dried over sodium sulfate. The crude product is purified by chromatography on silica gel (eluent: dichloromethane with increasing methanol content). 1.40 g (88% of theory) of the desired compound are obtained.

Workup

  1. temperatureIt is then cooled in an ice bath
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customThe crude product is purified by chromatography on silica gel (eluent: dichloromethane with increasing methanol content)

Sources & evidence

ORD record
ord-97221fbc8dd94c17b07c9506c70f0fd6
Source dataset
uspto-grants-2012_02
Patent number
US08114400B2

Reaction notes

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