Ammonia → HCID 178494684, compound

HRID 50378

Reaction equation

HRID 50378 reaction equation
Cl.COC[C:5]([O:7][CH2:8][CH:9]=[NH:10])=O.[OH:11][CH2:12][C:13]([CH2:15]O)=O.[NH3:17]>C(Cl)Cl>[OH:11][CH2:12][C:13]1[N:17]=[C:9]([CH2:8][O:7][CH3:5])[NH:10][CH:15]=1

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 670DihydroxyacetoneHCID 57478929Iminoethyl methoxyacetate hydrochloride

Product 1

HCID 178494684HCID 178494684, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
68 °C

Procedure

A mixture of 30.6 g (0.20 mol) of iminoethyl methoxyacetate hydrochloride, 18 g (0.20 mol) of 1,3-dihydroxyacetone and 200 mL of liquid ammonia was heated to 68° C. for 3 hours in a stirred autoclave at a pressure of 27 bar (analogously to: P. Dziuron et al., Arch. Pharm. 307, 1974, p.470). Then the ammonia was eliminated and 200 mL of methylene chloride were added. The white precipitate formed was filtered off and washed with methylene chloride. The filtrate was evaporated down and the residue obtained was purified by chromatography (aluminium oxide; methylene chloride/ethanol=90:10 to 85:15). Yield: 26.7 g (94% of theory), C6H10N2O2 (142.20); Rf value: 0.43 (silica gel; methylene chloride/ethanol=9:1); mass spectrum: (M)+=142.

Workup

  1. customThe white precipitate formed
  2. filtrationwas filtered off
  3. washwashed with methylene chloride
  4. customThe filtrate was evaporated down
  5. customthe residue obtained
  6. customwas purified by chromatography (aluminium oxide; methylene chloride/ethanol=90:10 to 85:15)

Sources & evidence

ORD record
ord-7e21ca4540c6429c96d42769f9678dad
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Linked notes

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