Formaldehyde → HCID 19101372, compound

HRID 1886157Notes

Reaction equation

HRID 1886157 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].[CH2:7]=O.[CH:9]1[CH2:13][CH:12]=[CH:11][CH:10]=1>O.C(Cl)Cl>[CH:10]12[CH2:9][CH:13]([CH:12]=[CH:11]1)[CH2:7][N:2]2[CH2:3][C:4]([NH2:6])=[O:5]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 7612CyclopentadieneHCID 2723639Glycinamide hydrochloride

Product 1

HCID 19101372HCID 19101372, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

A solution of glycinamide hydrochloride 22.1 g, 0.20 mol) in water is treated with 37% formalin (23.0 g, 0.28 mol formaldehyde) cooled to 10° C., treated with cyclopentadiene (26.4 g, 0.40 mol), stirred for 3 hours at 5°-10° C., and diluted with methylene chloride. The phases are separated. The aqueous phase is extracted with methylene chloride and basified with 10% NaOH to pH 12 with cooling. The aqueous basic phase is extracted with methylene chloride. The methylene chloride extracts of the basic aqueous phase are combined and concentrated in vacuo to give the title product (N-carboxamidomethylazanorbornene) as a solid, 17.6 g, mp 74°-96° C. which can be purified by sublimation at 120° C./0.55 torr. The compound is identified by NMR and mass spectral analyses.

Workup

  1. customThe phases are separated
  2. extractionThe aqueous phase is extracted with methylene chloride and basified with 10% NaOH to pH 12
  3. temperaturewith cooling
  4. extractionThe aqueous basic phase is extracted with methylene chloride
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f646989c594b4599966f81c535d8bfe6
Source dataset
uspto-grants-1992_09
Patent number
US05149825

Reaction notes

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