Hexamethylenetetramine → HCID 57845555, compound

HRID 734646Notes

Reaction equation

HRID 734646 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)=[O:4].C1N2CN3CN(C2)C[N:15]1C3>ClC1C=CC=CC=1.C(OCC)C>[NH2:15][CH2:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)=[O:4]

Participants

5

Reactant 2

HCID 4101HexamethylenetetramineHCID 578455522-Bromo-1-(6-nitro-3-pyridinyl)ethanone

Product 1

HCID 57845555HCID 57845555, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7964ChlorobenzeneSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 1.549 g (6.322 mmol) of 2-bromo-1-(6-nitropyridin-3-yl)ethanone in 25 cm3 of chlorobenzene is added at a temperature in the region of 20° C. to a solution of 0.975 g (6.954 mmol) of hexamethylenetetraamine in 10 cm3 of chlorobenzene. After stirring for 1 hour at this temperature, the suspension is heated for 18 hours at 50° C. The reaction medium is then cooled to 5° C. and then diluted with 200 cm3 of ethyl ether. The precipitate thus obtained is filtered and washed with three times 50 cm3 of ethyl ether. The resulting ammonium salt is stirred in 20 cm3 of ethanol and then 8 cm3 of 37% hydrochloric acid are added at a temperature in the region of 20° C. The solution is then stirred for 16 hours at this temperature. The precipitate formed is filtered, washed with three times 50 cm3 of water, drained and dried to give 1.05 g of 2-amino-1-(6-nitropyridin-3-yl)ethanone in the form of a cream powder. ES+: m/z=182 (MH+).

Workup

  1. temperatureThe reaction medium is then cooled to 5° C.
  2. customThe precipitate thus obtained
  3. filtrationis filtered
  4. washwashed with three times 50 cm3 of ethyl ether
  5. stirringThe resulting ammonium salt is stirred in 20 cm3 of ethanol
  6. addition8 cm3 of 37% hydrochloric acid are added at a temperature in the region of 20° C
  7. stirringThe solution is then stirred for 16 hours at this temperature
  8. customThe precipitate formed
  9. filtrationis filtered
  10. washwashed with three times 50 cm3 of water
  11. customdried

Sources & evidence

ORD record
ord-702daee199d5495395695369542e1a31
Source dataset
uspto-grants-2009_09
Patent number
US07592365B2

Reaction notes

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