Methane → HCID 21449080, compound

HRID 596883Notes

Reaction equation

HRID 596883 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13]([C:15](=[NH:18])OC)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[ClH:19].[CH3:20][O:21][CH:22]([O:25][CH3:26])[CH2:23][NH2:24].C>CO>[ClH:19].[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[O:14][C:13]([C:15]([NH2:18])=[N:24][CH2:23][CH:22]([O:25][CH3:26])[O:21][CH3:20])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 89728Aminoacetaldehyde dimethyl acetalHCID 21449082HCID 21449082, compound

Product 1

HCID 21449080HCID 21449080, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 30 g (0.12 mole) of methyl 5-(4-acetylphenyl)-2-furimidate and 500 ml of saturated ethereal/HCl was stirred for 2 hrs. at room temperature and the resulting solid filtered. A mixture of this solid, 12.6 g (0.12 mole) of aminoacetaldehyde dimethyl acetal and 500 ml of methanol was refluxed for 3 hr. with the resulting solution being treated with Darco and filtered hot. The filtrate was taken to dryness on the Calab evaporator yielding a residual solid. This solid was dissolved in refluxing methanol (Darco), filtered and the filtrate cooled to room temperature. The filtrate was diluted with ether and the resulting solid filtered and air dried to yield 24 g (57%) of 5-(4-acetylphenyl)-N'-2,2-dimethoxyethyl-2-furamidine hydrochloride.

Workup

  1. filtrationat room temperature and the resulting solid filtered
  2. temperaturewas refluxed for 3 hr
  3. filtrationfiltered hot
  4. customThe filtrate was taken to dryness on the Calab evaporator
  5. customyielding a residual solid
  6. dissolutionThis solid was dissolved
  7. filtrationfiltered
  8. additionThe filtrate was diluted with ether
  9. filtrationthe resulting solid filtered
  10. customair dried

Sources & evidence

ORD record
ord-0793602fca074ca9831e1ad6bf438b5a
Source dataset
uspto-grants-1977_03
Patent number
US04012414

Reaction notes

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