Formaldehyde → N-Acetyl-N-methylglycine
Reaction equation
[CH3:1][NH:2][C:3](=[O:5])[CH3:4].[C]=[O:7].C=O.[O:10]1[CH2:14][CH2:13]CC1>>[C:3]([N:2]([CH2:13][C:14]([OH:10])=[O:7])[CH3:1])(=[O:5])[CH3:4]Participants
Conditions
- Temperature
- 130 °C
Procedure
A 1 L autoclave was charged with N-methylacetamide (IX) (90 g, 1.23 mole), Co(OAc)2.4H2O (16.5 g, 0.13 mole), and tetrahydrofuran (500 mL). After sealing the autoclave, 2200 psi (15,172 kPa) of CO:H2 (70:30) was established at 25° C. with stirring at 2000 rpm. The contents of the autoclave were heated to 130° C. and 3200 psi (22,069 kPa) CO:H2 (70:30) was established. After approximately one hour, rapid gas uptake was observed. The reaction mass was cooled to 65° C. and the pressure was slowly reduced to 1500 psi (10,345 kPa). At this point carbon monoxide was established as the carboxymethylation feed gas. Under a constant 1500 psi (10,345 kPa), 47 Wt. % formalin (180 mL, 2.97 mole) was delivered at 6 mL/min. The reaction was stirred at 65° 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 (XX). This resulted in an 85% yield of (XX).
Workup
- customwas established at 25° C.
- temperatureThe reaction mass was cooled to 65° C.
- stirringThe reaction was stirred at 65° C. for 30 min.
- temperatureThen the reaction was cooled to 25° C.
- customremoved from the autoclave
Sources & evidence
- ORD record
- ord-91874ea73fbf45568898207589a5d95e
- Source dataset
- uspto-grants-2004_07
- Patent number
- US06759549B2
Reaction notes
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