Chloroacetaldehyde → HCID 121409853, compound

HRID 64541Notes

Reaction equation

HRID 64541 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[C:5]([NH:11][C:12](=[NH:21])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[C:4]([CH:22]([CH3:24])[CH3:23])[CH:3]=1.Cl[CH2:26][CH:27]=O.C(=O)(O)[O-].[Na+].CC(O)C>O>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[C:5]([N:11]2[CH:27]=[CH:26][N:21]=[C:12]2[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[C:4]([CH:22]([CH3:24])[CH3:23])[CH:3]=1

Participants

6

Reactant 4

HCID 33ChloroacetaldehydeHCID 3776IsopropanolHCID 516892Sodium BicarbonateHCID 178490390HCID 178490390, compound

Product 1

HCID 121409853HCID 121409853, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 500 ml round bottom flask was charged with N-(4-bromo-2,6-diisopropylphenyl)-3-methoxybenzimidamide (19.73 g, 50.7 mmol), 2-chloroacetaldehyde (12.83 ml, 101 mmol), sodium bicarbonate (12.77 g, 152 mmole) and 2-Propanol (300 ml). The reaction was allowed to reflux for 16 hours. The reaction mixture was diluted with deionized water and extracted with ethyl acetate, the organic portion was combined and subjected to a column chromatography (SiO2 gel; 20% THF in heptane) to yield the desired product (16.47 g, 79%).

Workup

  1. temperatureto reflux for 16 hours
  2. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-a1efcba54b9e4d599f4725d702cabc32
Source dataset
uspto-grants-2016_09
Patent number
US09450195B2

Reaction notes

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