4-Chlorobenzaldehyde → HCID 59235218, compound

HRID 1919785Notes

Reaction equation

HRID 1919785 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].S([O-])([O-])(=O)=O.[Mg+2].[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1>ClCCl>[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[N:1][CH:2]([C:7]2[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=2)[C:3]([O:5][CH3:6])=[O:4])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 13617480HCID 13617480, compound

Product 1

HCID 59235218HCID 59235218, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

998 mg of methyl 2-amino-2-(4-methoxyphenyl)acetate (prepared according to M. A. Sierra Rodrigez et al, Int. Pat. Appl. WO 02/102762) are dissolved in 30 mL of dichloromethane. 1 g of magnesium sulphate is added along with 717 mg of 4-chlorobenzaldehyde. The mixture is stirred at AT for 21 hours, the solid is filtered off, the filtrate is washed with dichloromethane then the solvent is dried over magnesium sulphate and evaporated to produce 1.65 g of an oil. The crude product is purified by chromatography over silica gel while eluting with the 90/10/1 then 80/20/1 heptane/ethyl acetate/triethylamine mixture. 1.24 g of colourless oil is obtained which crystallises on cooling (Yd=76%).

Workup

  1. filtrationthe solid is filtered off
  2. washthe filtrate is washed with dichloromethane
  3. dry with materialthe solvent is dried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-b3363a23f69248a7899a350babe5410a
Source dataset
uspto-grants-2012_05
Patent number
US08168667B2

Reaction notes

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