Formamidine acetate → HCID 178478070, compound

HRID 1159188Notes

Reaction equation

HRID 1159188 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]([NH2:13])[CH2:11][NH2:12])=[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]([CH2:8][CH2:9][CH:10]2[CH2:11][NH:12][CH:14]=[N:13]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 686441294-(4-Chlorophenyl)-1,2-butanediamine

Product 1

HCID 178478070HCID 178478070, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(4-chlorophenyl)-1,2-butanediamine (0.084 mg, 0.42 mmol) in ethanol (8 ml) was added formamidine acetate (0.15 g, 1.45 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 an off-white amorphous solid (0.041 g, 47%); MS (ISP): 209.3 ((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-7b7a05b7adbf464cb4e551a4ed6c8e5c
Source dataset
uspto-grants-2010_10
Patent number
US07812047B2

Reaction notes

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