Water → HCID 178423707, compound

HRID 1080731Notes

Reaction equation

HRID 1080731 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14](=O)[CH2:15]Br)=[CH:4][CH:3]=1.C(O)(=O)C.[CH:22]([NH2:24])=[NH:23].O>C(N)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[N:23]=[CH:22][NH:24][CH:15]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 160693Formamidine acetateHCID 23365458HCID 23365458, compound

Product 1

HCID 178423707HCID 178423707, compoundYield 24.6%

Reagents, catalysts & solvents 1

HCID 713FormamideSolvent

Procedure

A vigorously stirred solution of 1.0 g (3.5 mmol) of 4-methyl-2'-bromoacetyl-1,1'-biphenyl and 1.86 g of formamidine acetate in 10 mL of formamide was heated at 150° C. for 6 hours. The reaction mixture was cooled, poured into 100 mL of water and the resultant mixture extracted several times with ether. The combined extracts were washed with water (3×), dried over magnesium sulfate, filtered and evaporated under vacuum. The residue was purified by chromatography over silica gel, eluting with hexane/ethyl acetate (1:1) to yield 200 mg (0.86 mmol, 24%) of the product. FAB-MS (Li spike): calculated for C16H14N2 234; found 241 (M+Li). 1H NMR (200 MHz, CDCl3); 2.34 (s, 3H), 6.61 (s, 1H), 7.10 (m, 4H), 7.30 (m, 3H), 7.48 (s, 1H), 7.68 (dd, 1H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionthe resultant mixture extracted several times with ether
  3. washThe combined extracts were washed with water (3×)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customThe residue was purified by chromatography over silica gel
  8. washeluting with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-7ccd70042e7a4c4da588135191bfc7ad
Source dataset
uspto-grants-1996_12
Patent number
US05583130

Reaction notes

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