Formaldehyde → HCID 13390719, compound

HRID 464575Notes

Reaction equation

HRID 464575 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH2:5][NH:6][C:7]([O:9][CH3:10])=[O:8])[CH3:2].C=O.[C:14](OC(=O)C)(=O)C.[P:21]([O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[O:22]C1C=CC=CC=1>C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:11])[CH2:5][N:6]([C:7]([O:9][CH3:10])=[O:8])[CH2:14][P:21]([O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:22])[CH3:2]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 7540Triphenyl phosphiteHCID 7918Acetic AnhydrideHCID 235150Ethyl N-(methoxycarbonyl)glycinate

Product 1

HCID 13390719HCID 13390719, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of N-carbomethoxy glycine ethyl ester (10.0 g, 0.06 mole), paraformaldehyde (2.0 g, 0.06 mole), acetic anhydride (96%, 4.0 g, 0.06 mole) and acetic acid (20 ml) was stirred for 3 hrs. at 60°-70° C. under nitrogen. Triphenyl phosphite (19.2 g, 0.03 mole) was slowly added then the reaction mixture was refluxed for 2 hrs. at 110°-200° C. The reaction was cooled and the solvent was evaporated under vacuum. The resulting oily material was dissolved in chloroform and washed with water. The product was confirmed by nmr. Yield 70.5%.

Workup

  1. customat 60°-70° C.
  2. temperaturethe reaction mixture was refluxed for 2 hrs
  3. customat 110°-200° C
  4. temperatureThe reaction was cooled
  5. customthe solvent was evaporated under vacuum
  6. dissolutionThe resulting oily material was dissolved in chloroform
  7. washwashed with water

Sources & evidence

ORD record
ord-5975d282451d4cb1a0820dc0751e04fe
Source dataset
uspto-grants-1985_10
Patent number
US04548760

Reaction notes

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