Ammonia → HCID 178494684, compound

HRID 2288515Notes

Reaction equation

HRID 2288515 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), Rf value: 0.43 (silica gel; methylene chloride/ethanol=9:1) C6H10N2O2 (142.20) 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-ad4dc04c0b564452a093e5cd5f840121
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

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