Acetamide → N-acetyliminodiacetic acid

HRID 1386852Notes

Reaction equation

HRID 1386852 reaction equation
[C:1](N)(=[O:3])[CH3:2].C=O.O.Cl.[NH:9]([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][C:11]([OH:13])=[O:12].C(NCC(O)=O)(=O)C>COCCOC>[C:1]([N:9]([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][C:11]([OH:13])=[O:12])(=[O:3])[CH3:2]

Participants

8

Reactant 6

HCID 178AcetamideHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 962WaterHCID 8897Iminodiacetic acidHCID 10972Acetylglycine

Product 1

HCID 10130190N-acetyliminodiacetic acidYield 87%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
110 °C

Procedure

A 300 mL autoclave was charged with acetamide (VII) (11.8 g, 0.2 mole), 95% paraformaldehyde (13.6 g, 0.43 mole), water (12.9 g, 0.72 mole), 37% HCl (1.8 g, 0.018 mole), DME (90 mL), and Co2(CO)8 (4.1 g, 0.012 mole) and pressurized to 1500 psi (10,345 kPa) CO at 25° C. This mixture was heated to 110° C. for 30 minutes. HPLC analysis of this stream gave an 87% yield of (XVI), 0.5% iminodiacetic acid (XIV), and 4.0% N-acetylglycine (XVIII).

Workup

  1. custompressurized to 1500 psi (10,345 kPa) CO at 25° C

Sources & evidence

ORD record
ord-c9073c61aeae4f8ba1c24cf8501c2fab
Source dataset
uspto-grants-2001_07
Patent number
US06265605B1

Reaction notes

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