Formaldehyde → HCID 69898620, compound

HRID 2415647Notes

Reaction equation

C=O.C([N:10]1[C:14](=[O:15])[CH:13]=[CH:12][C:11]1=O)C1C=CC=CC=1.[CH2:17]([NH:24][CH2:25][C:26]([OH:28])=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O.[C:30]1([CH3:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH2:36]([C:13]12[CH2:12][CH2:11][C:26](=[O:28])[CH:25]1[N:24]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[NH:10][C:14]2=[O:15])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

Reactant 5

HCID 712Formaldehyde

HCID 962Water

HCID 1140Toluene

HCID 74204Benzylmaleimide

HCID 869652-(Benzylamino)acetic acid

Product 1

HCID 69898620HCID 69898620, compoundYield 78%

Procedure

Paraformaldehyde (13.5 g) was added to a solution of N-benzylmaleimide (10.8 g; 60 mmol) and N-benzylglycine (9.9 g; 60 mmol) in toluene (400 mL) and the resulting mixture was refluxed with azeotropic removal of water, for 10 hours. The mixture was cooled to room temperature and was concentrated in vacuo. The mixture was purified by flash chromatography (30% EtOAc in hexane) to afford 15 g (78%) of the title product (I-1 a), as an amorphous solid.

Workup

concentrationwas concentrated in vacuo
customThe mixture was purified by flash chromatography (30% EtOAc in hexane)

Sources & evidence

ORD record: ord-867cb5834fd6445a93bb4c34328676c8
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06821964B2

Reaction notes

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