Formaldehyde → HCID 11075463, compound

HRID 248574Notes

Reaction equation

HRID 248574 reaction equation
Cl.[NH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5].C=O.[CH3:10][CH:11]1[C:15]([CH3:16])=[C:14]([CH3:17])[C:13]([CH3:18])=[C:12]1[CH3:19].N[CH2:21]C(OC)=O>C(O)(=O)C.O>[CH3:18][C:13]1([CH2:21][NH:2][CH2:3][C:4]([O:6][CH3:7])=[O:5])[C:12]([CH3:19])=[C:11]([CH3:10])[C:15]([CH3:16])=[C:14]1[CH3:17]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 69221Glycine methyl esterHCID 776671,2,3,4,5-PentamethylcyclopentadieneHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 11075463HCID 11075463, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

To a stirred mixture of methyl glycinate hydrochloride (6.28 g, 0.05 mole) in 30 mL of glacial acetic acid and 37% aqueous formaldehyde (4.1 g, 1.5 g real, 0.05 mole) is added pentamethylcyclopentadiene (6.81 g, 0.05 mole) after all of the solid methyl glycinate has dissolved. A light brown solution is initially obtained. The temperature is kept at 35° C. for five minutes with ice-bath cooling to control the exotherm. The color of the solution changes to light purple and the temperature is then kept at 33° C. for about 6 hours. This reaction mixture is combined with 100 mL of water and the aqueous phase is extracted with two×20 mL portions of methylene chloride The clear aqueous phase is then treated with 50% sodium hydroxide, with cooling to maintain a temperature of 35° C., to pH 12. The basic aqueous phase is extracted with two×30 mL portions of methylene chloride. The organic layer is concentrated in vacuo to give approximately 5.0 g of the title compound. Yield is 40%, about 80% purity, of the product which is identified by proton nuclear magnetic resonance, carbon-13 nuclear magnetic resonance and electron impact mass spectral analyses.

Workup

  1. dissolutionhas dissolved
  2. customA light brown solution is initially obtained
  3. temperaturecooling
  4. waitThe color of the solution changes to light purple and the temperature is then kept at 33° C. for about 6 hours
  5. extractionthe aqueous phase is extracted with two×20 mL portions of methylene chloride The clear aqueous phase
  6. additionis then treated with 50% sodium hydroxide
  7. temperaturewith cooling
  8. extractionThe basic aqueous phase is extracted with two×30 mL portions of methylene chloride
  9. concentrationThe organic layer is concentrated in vacuo

Sources & evidence

ORD record
ord-b511457ed4f445a582af6d12696c5d61
Source dataset
uspto-grants-1993_05
Patent number
US05210277

Reaction notes

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