Formaldehyde → HCID 86610207, compound

HRID 1008861Notes

Reaction equation

HRID 1008861 reaction equation
[N:1]1([CH:8]=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH2:10]=O.[F:12][C:13]([F:23])([F:22])[C:14]1[CH:15]=[C:16]([C:20]#[CH:21])[CH:17]=[CH:18][CH:19]=1>O1CCOCC1.C(OCC)(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Cu+2]>[F:12][C:13]([F:22])([F:23])[C:14]1[CH:15]=[C:16]([C:20]#[C:21][CH2:10][N:4]2[CH2:5][CH2:6][CH2:7][N:1]([CH:8]=[O:9])[CH2:2][CH2:3]2)[CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 3

HCID 712FormaldehydeHCID 27784901-Ethynyl-3-(trifluoromethyl)benzeneHCID 70066561,4-diazepane-1-carbaldehyde

Product 1

HCID 86610207HCID 86610207, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of 1.28 g (10 mmol) of 1,4-diazepane-1-carbaldehyde and 0.33 g (11 mmol) of paraformaldehyde in 13 ml of dioxane is heated at 80° C. until a homogeneous solution is obtained. 1.70 g (10 mmol) of 3-trifluoromethylphenylacetylene in solution in 7 ml of dioxane and 1.81 g (10 mmol) of copper diacetate are added. The mixture is heated at 80° C. for 4 hours. It is cooled to ambient temperature and diluted with 75 ml of ethyl acetate. The organic phase is washed with 25 ml of 30% ammonia solution and with saturated aqueous sodium chloride solution. It is dried over sodium sulphate and evaporated to dryness. The residue is purified by chromatography on silica gel, eluting with a 98/2/0.2 then 96/4/0.4 and 94/6/0.6 mixture of dichloromethane, methanol and 30% ammonia, to give 2.67 g of product in the form of a yellow oil.

Workup

  1. customis obtained
  2. temperatureThe mixture is heated at 80° C. for 4 hours
  3. temperatureIt is cooled to ambient temperature
  4. washThe organic phase is washed with 25 ml of 30% ammonia solution and with saturated aqueous sodium chloride solution
  5. dry with materialIt is dried over sodium sulphate
  6. customevaporated to dryness
  7. customThe residue is purified by chromatography on silica gel
  8. washeluting with a 98/2/0.2
  9. addition96/4/0.4 and 94/6/0.6 mixture of dichloromethane, methanol and 30% ammonia

Sources & evidence

ORD record
ord-e2ff5a55c1744b52960ddd04e2b6b19a
Source dataset
uspto-grants-2011_07
Patent number
US07973042B2

Reaction notes

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