Formamidine acetate → HCID 178478224, compound

HRID 1159191Notes

Reaction equation

HRID 1159191 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][CH:8]([NH2:11])[CH2:9][NH2:10])=[CH:4][CH:3]=1.[C:14](O)(=O)C.C(N)=N>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH:8]2[CH2:9][NH:10][CH:14]=[N:11]2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 68644081HCID 68644081, compound

Product 1

HCID 178478224HCID 178478224, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(4-chloro-phenoxy)-propane-1,2-diamine (0.19 g, 0.95 mmol) in ethanol (5 ml) was added formamidine acetate (0.1 g, 1.0 mmol) and the mixture was stirred overnight at room temperature. The solvent was evaporated, water (5 ml) was added and the mixture was extracted 3 times with dichloromethane (10 ml). The combined organic layers were dried over magnesium sulfate and evaporated. The residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent:ethyl acetate/methanol=90:10) to yield a light yellow oil (0.063 g, 32%); MS (ISP): 211.2 ((M+H)+).

Workup

  1. customThe solvent was evaporated
  2. additionwater (5 ml) was added
  3. extractionthe mixture was extracted 3 times with dichloromethane (10 ml)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent:ethyl acetate/methanol=90:10)

Sources & evidence

ORD record
ord-bec805fdbb6d4f5db55c4dc9a5ef19af
Source dataset
uspto-grants-2010_10
Patent number
US07812047B2

Reaction notes

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