Pyridine → [(5-Chloro-2-formyl-phenylcarbamoyl)methyl] phosphonic acid diethyl ester

HRID 1018905Notes

Reaction equation

HRID 1018905 reaction equation
N1C=CC=CC=1.[NH2:7][C:8]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:9]=1[CH:10]=[O:11].[CH2:17]([O:19][P:20]([CH2:25][C:26](Cl)=[O:27])(=[O:24])[O:21][CH2:22][CH3:23])[CH3:18]>C1(C)C=CC=CC=1>[CH2:22]([O:21][P:20]([CH2:25][C:26](=[O:27])[NH:7][C:8]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:9]=1[CH:10]=[O:11])(=[O:24])[O:19][CH2:17][CH3:18])[CH3:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10822542HCID 10822542, compoundHCID 112521382-Amino-4-chlorobenzaldehyde

Product 1

HCID 15511750[(5-Chloro-2-formyl-phenylcarbamoyl)methyl] phosphonic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Pyridine (3.7 ml, 45.7 mmol) is added to a solution of 2-amino-4-chlorobenzaldehyde (6.18 g, 39.7 mmol) in 170 ml of anhydrous toluene, followed dropwise by a solution of chlorocarbonylmethylphosphonic acid diethyl ester (9.8 g, 45.7 mmol) in 15 ml of anhydrous toluene whilst maintaining the reaction mixture at a temperature of less than 30° C. When the addition is complete, the mixture is stirred for 1 hour at room temperature. The reaction mixture is washed several times with water and then with a 1N HCl solution, and then again with water. Finally the mixture is washed with an aqueous saturated NaCl solution. The organic phase is dried over MgSO4, and filtration is carried out, followed by evaporation to obtain the expected crude product in the form of an orange oil. The crude product is used in the following step.

Workup

  1. temperaturewhilst maintaining the reaction mixture at a temperature of less than 30° C
  2. additionWhen the addition
  3. washThe reaction mixture is washed several times with water
  4. washFinally the mixture is washed with an aqueous saturated NaCl solution
  5. dry with materialThe organic phase is dried over MgSO4, and filtration
  6. customfollowed by evaporation

Sources & evidence

ORD record
ord-f5714da919194e1fa4d37633a02e6db5
Source dataset
uspto-grants-2002_11
Patent number
US06486143B2

Reaction notes

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