Triethylamine → HCID 2096879, compound

HRID 1466417Notes

Reaction equation

HRID 1466417 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].[Br:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=1.C(N(CC)CC)C>C1COCC1>[Br:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH:5][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[Cl:1])=[O:16])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 666482-ChlorobenzylamineHCID 685154-Bromobenzoyl chloride

Product 1

HCID 2096879HCID 2096879, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 2-chlorobenzylamine (2.42 mL, 20 mmol) in THF (80 mL, anhyd) at 0° C. added a solution of 4-bromobenzoyl chloride (4.39 g, 20 mmol) in THF (20 mL, anhyd.) and then triethylamine (2.93 mL, 21 mmol). After 12 h the resulting mixture was filtered and the solids rinsed with EtOAc. The combined filtrates were diluted with EtOAc (100 mL), washed with 1N HCl, satd NaHCO3 and brine, then dried (anhyd Na2SO4) and concentrated to afford the title compound (6.36 g, 98%) as a white solid, which was used in the next step without purification. GC-MS (EI): 322, 324.

Workup

  1. filtrationAfter 12 h the resulting mixture was filtered
  2. washthe solids rinsed with EtOAc
  3. additionThe combined filtrates were diluted with EtOAc (100 mL)
  4. washwashed with 1N HCl
  5. dry with materialdried (anhyd Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c09a182339464b2e961c348c934c8170
Source dataset
uspto-grants-2015_04
Patent number
US09000022B2

Reaction notes

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