Acetamide → N-acetyliminodiacetic acid

HRID 1859254Notes

Reaction equation

HRID 1859254 reaction equation
[C:1]([NH2:4])(=[O:3])[CH3:2].[CH2:5]1[CH2:9][O:8]CC1.C=[O:11].N[CH2:13][C:14]([OH:16])=[O:15]>C(O)(=O)C>[C:1]([N:4]([CH2:5][C:9]([OH:8])=[O:11])[CH2:13][C:14]([OH:16])=[O:15])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 178AcetamideHCID 712Formaldehyde2×HCID 750GlycineHCID 8028Tetrahydrofuran

Product 1

HCID 10130190N-acetyliminodiacetic acidYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A 2 L autoclave was charged with acetamide (VII)(129.8 g, 2.2 mole), THF (1 L), and acetic acid (45 g) and was purged with argon for 10 min. Under the argon purge, Co2 (CO)8 (20.9 g, 0.06 mole) was added. After sealing the autoclave, 150 psi (1034 kPa) of CO:H2 (95:5) was established at 25° C. and was slowly vented. Then 2200 psi (15,172 kPa) of CO:H2 (95:5) was established at 25° C. with stirring at 2000 rpm. The contents of the autoclave were heated to 100° C. and 3200 psi (22,069 kPa) CO:H2 (95:5) was established. Under a constant 3200 psi (22,069 kPa), 47 Wt. % formalin (320 mL, 5.28 mole) was delivered at 40 mL/min. The reaction was stirred at 100° C. for 52 min. after the formalin addition was complete. Then the reaction was cooled to 25° C., removed from the autoclave, and assayed for N-acetyliminodiacetic acid. This resulted in a 95% yield of (XVI) and 1% glycine.

Workup

  1. customwas purged with argon for 10 min
  2. customUnder the argon purge
  3. additionCo2 (CO)8 (20.9 g, 0.06 mole) was added
  4. customwas established at 25° C.
  5. customwas established at 25° C.
  6. stirringThe reaction was stirred at 100° C. for 52 min.
  7. temperatureThen the reaction was cooled to 25° C.
  8. customremoved from the autoclave

Sources & evidence

ORD record
ord-a771fbb604c845d398ee6a6e1588f8cb
Source dataset
uspto-grants-2000_11
Patent number
US06153753

Reaction notes

Loading…