Cyanuric chloride → HCID 15616556, compound

HRID 986917Notes

Reaction equation

HRID 986917 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].C(N(C(C)C)CC)(C)C.[C:19]1([C@@H:25]([NH2:27])[CH3:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[Cl:9][C:8]1[N:1]=[C:2]([Cl:3])[N:4]=[C:5]([NH:27][C@H:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:26])[N:7]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 758181-Phenethylamine, (-)-HCID 81531Diisopropylethylamine

Product 1

HCID 15616556HCID 15616556, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of cyanuric chloride (25.0 g, 0.135 mol), diisopropylethylamine (17.5 g, 0.135 mol) in THF (500 mL) at 0° C. was added dropwise a solution of (1S)-1-phenylethylamine (16.4 g, 0.135 mol) in THF (100 mL) while maintaining the reaction temperature at or near 0° C. The reaction mixture was allowed to warm to ambient temperature then was concentrated under reduced pressure. The residue was dissolved in EtOAc (500 mL) and extracted with 1 N HCl (250 mL), H2O (250 mL) and brine (250 mL). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the titled compound as a white solid (35 g, 96%) MP 146-147° 1H NMR (CDCl3) δ 7.39 (m, 5H), 6.40 (b d, 1H), 5.25 (m, 1H), 1.59 (d, 3H); MS (ESI+) (M+) 269.1 obs.

Workup

  1. temperatureto warm to ambient temperature
  2. concentrationthen was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc (500 mL)
  4. extractionextracted with 1 N HCl (250 mL), H2O (250 mL) and brine (250 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-720c1211ed794bd9b9224943434c3181
Source dataset
uspto-grants-2003_10
Patent number
US06630469B2

Reaction notes

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