Acetamide → N-acetyliminodiacetic acid

HRID 1883245Notes

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: 100 °C

Procedure

The regenerated catalyst precursor was transferred, under CO:H2 pressure, into the autoclave containing CO:H2 (95:5) at 800 psi (5517 kPa), acetamide (VII) (29.5 g, 0.5 mole), 95% paraformaldehyde (34.0 g, 1.08 mole), water (32.2 g, 1.79 mole), and DME (650 mL). A CO:H2 (95:5) atmosphere at 1500 psi (10,345 kPa) was immediately established. This mixture was heated to 100° C. The reaction warmed to 125° C. and was maintained at this temperature for one hour. HPLC analysis of this stream gave a 95% yield of (XVI), 2% (XIV), 2.5% (XVIII), and 0.5% N-methyliminodiacetic acid.

Workup

temperatureThe reaction warmed to 125° C.
temperaturewas maintained at this temperature for one hour

Sources & evidence

ORD record: ord-f918112be62e4373a7e9d2cd2228da44
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06759549B2

Reaction notes

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