Formaldehyde → benzyl 2-(N-methyleneamino)-2-methylpropanoate

HRID 377571Notes

Reaction equation

HRID 377571 reaction equation
[CH2:1]=O.[NH2:3][C:4]([CH3:16])([CH3:15])[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]>C(OCC)C>[CH2:1]=[N:3][C:4]([CH3:16])([CH3:15])[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 11116894Benzyl 2-amino-2-methylpropanoate

Product 1

HCID 19354575benzyl 2-(N-methyleneamino)-2-methylpropanoateYield 98.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

37% Aqueous formaldehyde solution (17.3 g) was added over 10 minutes to a stirred solution of benzyl 2-amino-2-methylpropanoate (28.0 g) in diethyl ether at ambient temperature. The two phase mixture was stirred for 21/2 hours then diluted with diethyl ether and washed with brine. The ethereal solution was dried (magnesium sulphate) and solvent evaporated under reduced pressure to give benzyl 2-(N-methyleneamino)-2-methylpropanoate (29.4 g) in equilibrium with its trimer 1,3,5-tri(1-benzyloxycarbonyl-1-methylethyl)hexahydrotriazine as a colourless oil, IR (liquid film) 2980(m), 1725(vs), 1250(m), 1135(vs).

Workup

  1. washwashed with brine
  2. dry with materialThe ethereal solution was dried (magnesium sulphate) and solvent
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a872f154ffd1449eaf40b5814a199c7a
Source dataset
uspto-grants-2000_02
Patent number
US06028032

Reaction notes

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