Benzoyl chloride → Methyl 2-benzamido-2-(dimethoxyphosphoryl)acetate

HRID 322933Notes

Reaction equation

HRID 322933 reaction equation
[NH2:1][CH:2]([P:7]([O:11][CH3:12])([O:9][CH3:10])=[O:8])[C:3]([O:5][CH3:6])=[O:4].[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl>[C:13]([NH:1][CH:2]([P:7]([O:11][CH3:12])([O:9][CH3:10])=[O:8])[C:3]([O:5][CH3:6])=[O:4])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 11084793Methyl 2-amino-2-(dimethoxyphosphoryl)acetate

Product 1

HCID 14104867Methyl 2-benzamido-2-(dimethoxyphosphoryl)acetateYield 46.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of methyl amino(dimethoxyphosphoryl)acetate (6 g) in dichloromethane (50 mL) is treated with benzoyl chloride (5 g) and the mixture allowed to stand at room temperature for 4 hours. The reaction mixture is washed twice with saturated aqueous sodium bicarbonate solution (75 mL), brine (50 mL), dried over magnesium sulphate and evaporated. The residual pale yellow oil is dissolved in ether (5 mL) and pentane added to give methyl benzoylamino(dimethoxyphosphoryl)acetate (4.25 g) as a white solid.

Workup

  1. washThe reaction mixture is washed twice with saturated aqueous sodium bicarbonate solution (75 mL), brine (50 mL)
  2. dry with materialdried over magnesium sulphate
  3. customevaporated
  4. dissolutionThe residual pale yellow oil is dissolved in ether (5 mL)
  5. additionpentane added

Sources & evidence

ORD record
ord-e1b3835f14a0462eb43341f7587aa39d
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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