Acetic Acid → N-Acetyl-N-methylglycine

HRID 1859250Notes

Reaction equation

[CH3:1][NH:2][C:3](=[O:5])[CH3:4].C=O.[C:8]([OH:11])(=[O:10])[CH3:9]>>[C:3]([N:2]([CH2:9][C:8]([OH:11])=[O:10])[CH3:1])(=[O:5])[CH3:4]

Participants

Reactant 3

HCID 176Acetic Acid

HCID 712Formaldehyde2×

HCID 6582N-Methylacetamide

Product 1

HCID 10975514N-Acetyl-N-methylglycineYield 92%

Conditions

Temperature: 85 °C

Procedure

A 1 L autoclave was charged with N-methylacetamide (IX) (160 g, 2.2 mole) , Co(OAc)2 ·4H2O (33 g, 0.13 mole), and acetic acid (1 L). After sealing the autoclave, 2200 psi (15,172 kPa) CO:H2 (70:30) was established at 25° C. with stirring at 2000 rpm. The contents of the autoclave were heated to 1300C and 3200 psi (22,069 kPa) CO:H2 (70:30) was established. After approximately 0.5 h, rapid gas uptake was observed. The reaction mass was cooled to 85° C. Under a constant 3200 psi (22,069 kPa) , 47 Wt. % formalin (180 mL, 2.97 mole) was delivered at 6 mL/min. The reaction was stirred at 85° C. for 30 min. after the formalin addition was complete. Then the reaction was cooled to 25° C., removed from the autoclave, and assayed for N-acetylsarcosine. This resulted in a 92% yield of (XX).

Workup

customwas established at 25° C.
stirringThe reaction was stirred at 85° C. for 30 min.
temperatureThen the reaction was cooled to 25° C.
customremoved from the autoclave

Sources & evidence

ORD record: ord-833437e9f43143a9964dbd17e5eb9a63
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06153753

Reaction notes

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