Acetamide → N-acetyliminodiacetic acid

HRID 1386853Notes

Reaction equation

[C:1](N)(=[O:3])[CH3:2].C=O.O.Cl.C(=O)=O.[NH:12]([CH2:17][C:18]([OH:20])=[O:19])[CH2:13][C:14]([OH:16])=[O:15].C(NCC(O)=O)(=O)C>COCCOC>[C:1]([N:12]([CH2:17][C:18]([OH:20])=[O:19])[CH2:13][C:14]([OH:16])=[O:15])(=[O:3])[CH3:2]

Participants

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) 1 (4. 1 g, 0.012 mole) and pressurized to 4000 psi (27,580 kPa) CO at 25° C. This mixture was heated to 110° C. for 30 min. HPLC analysis of this stream gave an 87% yield of (XVI), 0.5% (XIV), and 4.0% (XVIII).

Workup

custompressurized to 4000 psi (27,580 kPa) CO at 25° C

Sources & evidence

ORD record: ord-fb10aed3fba647fdb3b2ef314cbf2ff2
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265605B1

Reaction notes

Loading…