Aminoacetaldehyde dimethyl acetal → HCID 21449069, compound

HRID 596882Notes

Reaction equation

HRID 596882 reaction equation
[ClH:1].[C:2]1([C:8]2[O:12][C:11]([C:13](=[NH:16])OC)=[CH:10][CH:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[CH:19](OC)[CH2:20][NH2:21]>C(#N)C>[ClH:1].[C:2]1([C:8]2[O:12][C:11]([C:13]3[NH:16][CH:19]=[CH:20][N:21]=3)=[CH:10][CH:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 21449078HCID 21449078, compound

Product 1

HCID 21449069HCID 21449069, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 5-phenyl-2-furimidate hydrochloride (33 g, 0.14 mole), absolute alcohol (500 ml) and aminoacetaldehyde dimethyl acetal (15 g, 0.14 mole) was refluxed for 3 hr. The solvent was removed in a rotary evaporator and the residue was heated for 20 hr. at 63°-73° C with 3N HCl (400 ml). The solvent was decanted and the black viscous material was washed with water. It was purified by stirring with boiling acetonitrile and collected by filtration to give 4.1 g (9%). An analytical sample was prepared by recrystallization from acetonitrile m.p. >277° dec.

Workup

  1. temperaturewas refluxed for 3 hr
  2. customThe solvent was removed in a rotary evaporator
  3. temperaturethe residue was heated for 20 hr
  4. customat 63°-73° C
  5. customThe solvent was decanted
  6. washthe black viscous material was washed with water
  7. customIt was purified
  8. filtrationcollected by filtration
  9. customto give 4.1 g (9%)

Sources & evidence

ORD record
ord-6279061192e6488d83bf78e5be38846a
Source dataset
uspto-grants-1977_03
Patent number
US04012414

Reaction notes

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