Triethylamine → HCID 3415836, compound

HRID 745704Notes

Reaction equation

HRID 745704 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[Br:15][CH2:16][C:17](Br)=[O:18].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:17](=[O:18])[CH2:16][Br:15])[CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 61147Bromoacetyl bromideHCID 516892Sodium Bicarbonate

Product 1

HCID 3415836HCID 3415836, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of 3-aminopyridine (11 g.) and triethylamine (13.0 g.) in dry ethyl acetate (300 ml.) was added a solution of bromoacetyl bromide (26.0 g.) in dry ethyl acetate (26 ml.) over a period of 30 minutes with stirring at 0° to 5° C. and stirring was continued for an additional 2 hours at the same temperature. To the reaction mixture was added a chilled aqueous solution of sodium bicarbonate. After shaking well, the ethyl acetate layer was separated, washed successively with water, an aqueous solution of sodium bicarbonate and water, dried and then concentrated. There was obtained concentrate (200 ml.) containing the title compound. Thus obtained concentrate was used directly in the next step reaction without further purification.

Workup

  1. stirringstirring
  2. stirringAfter shaking well
  3. customthe ethyl acetate layer was separated
  4. washwashed successively with water
  5. dry with materialan aqueous solution of sodium bicarbonate and water, dried
  6. concentrationconcentrated
  7. customThere was obtained
  8. concentrationconcentrate (200 ml.)
  9. additioncontaining the title compound
  10. customThus obtained
  11. concentrationconcentrate
  12. customwas used directly in the next step reaction without further purification

Sources & evidence

ORD record
ord-a34f7e1a6cbd4d08be7f8af3860f2b24
Source dataset
uspto-grants-1986_07
Patent number
US04599426

Reaction notes

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