1,2-Dichloroethane → HCID 16244366, compound

HRID 2043327Notes

Reaction equation

HRID 2043327 reaction equation
ClC1C=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(O[BH-](O[C:19](=O)[CH3:20])OC(=O)C)(=O)C.[Na+].[C:23](O)(=O)[CH3:24].C(=O)(O)[O-].[Na+].Cl[CH2:33][CH2:34][Cl:35]>ClCCl>[Cl:35][C:34]1[CH:23]=[C:24]([NH:5][CH2:4][CH:6]2[CH2:7][CH2:8]2)[CH:19]=[CH:20][CH:33]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 79323-ChloroanilineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 16244366HCID 16244366, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloroaniline (1.27 g, 10 mmol) in 1,2-dichloroethane (20 ml) were added molecular sieves (4 g, size 0.4 nM) and cyclopropanecarboxyaldehyde (0.7 g, 10 mmol). After stirring the mixture for 5 min at room temperature sodium triacetoxyborohydride (3.18 g, 15 mmol) and acetic acid (0.6 g, 10 mmol) were added. The reaction mixture was stirred at room temperature overnight. For workup dichloromethane (100 ml) and 1 M sodium bicarbonate solution (40 ml) were added and the mixture was shaken. The organic layer was separated, dried over magnesium sulfate and evaporated. The residue was purified using flash chromatography (heptane/ethyl acetate=9:1) to yield a colourless liquid (1.09 g, 60%); MS (EI): 181.1 (M+.).

Workup

  1. additionwere added
  2. stirringthe mixture was shaken
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-49cd08961d8f433d91f6473ffda554f9
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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