Water → HCID 178488949, compound

HRID 745437

Reaction equation

HRID 745437 reaction equation
[C:1](OCC)(=[O:6])[CH2:2][C:3]([CH3:5])=O.[CH3:10][O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[NH:17])=[CH:14][CH:13]=1.O>C(Cl)(Cl)Cl>[OH:6][C:1]1[N:18]=[C:16]([C:15]2[CH:19]=[CH:20][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)[N:17]=[C:3]([CH3:5])[CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8868Ethyl AcetoacetateHCID 2290744-Methoxybenzenecarboximidamide

Product 1

HCID 178488949HCID 178488949, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Under N2, a solution of ethyl acetoacetate (7.15 g, 0.053 mol) in CHCl3 (200 ml) was added dropwise to a suspension of 4-methoxybenzamidine in CHCl3 (200 ml). After stirring at room temperature overnight, water was added to the solution. The aqueous phase was separated and extracted with CHCl3 and the organic layers were combined, dried (Na2SO4), filtered and concentrated to dryness. The residue was chromatographed on silica gel and the product was eluted with 2% CH3OH--CHCl3 to yield 8.58 g (75%) of product, m.p. 198°-199° C.

Workup

  1. customThe aqueous phase was separated
  2. extractionextracted with CHCl3
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was chromatographed on silica gel
  7. washthe product was eluted with 2% CH3OH

Sources & evidence

ORD record
ord-e992968ba96e4ce48b7d3fea3bb6058d
Source dataset
uspto-grants-1986_07
Patent number
US04598149

Linked notes

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