Acetamide → N-acetyliminodiacetic acid

HRID 1883246Notes

Reaction equation

[C:1](N)(=[O:3])[CH3:2].C=O.O.[NH:8]([CH2:13][C:14]([OH:16])=[O:15])[CH2:9][C:10]([OH:12])=[O:11].C(NCC(O)=O)(=O)C.CN(CC(O)=O)CC(O)=O>COCCOC>[C:1]([N:8]([CH2:13][C:14]([OH:16])=[O:15])[CH2:9][C:10]([OH:12])=[O:11])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 125 °C

Procedure

The regenerated catalyst precursor was transferred under CO:H2 pressure, into the autoclave at 95° C. containing CO:H2 (95:5) at 900 psi (6,210 kPa), acetamide (VII) (59.0 g, 1.0 mole), 95% paraformaldehyde (68.0 g, 2,16 mole), water (64.5 g, 3.60 mole) and DME (750 mL). A CO:H2 atmosphere (95:5) at 1500 psi (10,345 kPa) was immediately established. This mixture was heated to 125° C. and was maintained at this temperature for one hour. HPLC analysis of this stream gave a 77% yield of (XVI), 4% (XIV), 7.0% (XVIII), and 0.1% N-methyliminodiacetic acid.

Workup

temperaturewas maintained at this temperature for one hour

Sources & evidence

ORD record: ord-1ec726512105457480bb9433abbb711c
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06759549B2

Reaction notes

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