Acetamide → N-(Carboxymethyl)-N-(phosphonomethyl)glycine

HRID 542394Notes

Reaction equation

HRID 542394 reaction equation
[C:1]([N:4]([CH2:9][C:10]([OH:12])=[O:11])[CH2:5][C:6]([OH:8])=[O:7])(=O)C.C(N)(=O)C.[P:17]([OH:20])([OH:19])[OH:18].C=O>Cl>[P:17]([CH2:1][N:4]([CH2:9][C:10]([OH:12])=[O:11])[CH2:5][C:6]([OH:8])=[O:7])([OH:20])([OH:19])=[O:18]

Participants

6

Reactant 4

HCID 178AcetamideHCID 712Formaldehyde2×HCID 107909Phosphorous acidHCID 10130190N-acetyliminodiacetic acid

Product 1

HCID 80092N-(Carboxymethyl)-N-(phosphonomethyl)glycineYield 63%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A crude reaction mixture of N-acetyliminodiacetic acid was prepared from acetamide (5.90 g; 0.10 mol)) by the process described in French Pat. No. 2,523,576. This crude product was dissolved in a 20% aqueous hydrochloric acid solution and the resulting mixture was added to a 250 ml 3-necked flask equipped with an addition funnel and thermometer. Phosphorous acid (8.61 g; 0.105 mol) was added and the solution was heated to a temperature of 106° C.-107° C. When this temperature had been reached, formaldehyde (8.23 g of a 44% aqueous solution; 0.212 mole) was added to the mixture in the flask over a period of 30 minutes. After addition of formaldehyde was complete, the temperature was maintained at 106°-107° C. for an additional period of 3.5 hour. The reaction mixture was concentrated under reduced pressure and a precipitate formed. The product was collected by filtration to yield 14.4 g of N-phosphonomethyliminodiacetic acid (63% yield based on the starting amount of acetamide).

Workup

  1. additionthe resulting mixture was added to a 250 ml 3-necked flask
  2. customequipped with an addition funnel
  3. temperaturethe solution was heated to a temperature of 106° C.-107° C
  4. addition0.212 mole) was added to the mixture in the flask over a period of 30 minutes
  5. temperaturethe temperature was maintained at 106°-107° C. for an additional period of 3.5 hour
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. customa precipitate formed
  8. filtrationThe product was collected by filtration

Sources & evidence

ORD record
ord-c5e76f8a1a994444a628cec14edc4fd5
Source dataset
uspto-grants-1987_04
Patent number
US04657705

Reaction notes

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