Pentachloropyridine → HCID 12114314, compound

HRID 433955Notes

Reaction equation

HRID 433955 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[C:4](Cl)[C:3]=1[Cl:11].CCN(C(C)C)C(C)C.[NH2:21][C@@H:22]([CH3:25])[CH2:23][OH:24]>CC(O)C.CN(C1C=CN=CC=1)C>[Cl:8][C:6]1[C:5]([Cl:9])=[C:4]([NH:21][C@@H:22]([CH3:25])[CH2:23][OH:24])[C:3]([Cl:11])=[C:2]([Cl:1])[N:7]=1

Participants

6

Reactant 3

HCID 16584PentachloropyridineHCID 80307L-AlaninolHCID 81531Diisopropylethylamine

Product 1

HCID 12114314HCID 12114314, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3776IsopropanolSolvent

Procedure

To a solution of pentachloropyridine (30 g) in 2-propanol (300 ml) was added DIPEA (18 ml), DMAP (0.8 g) and (S)-(+)-2-amino-1-propanol (18 g), and the reaction mixture was heated under reflux for 18 h. After cooling, the reaction mixture was concentrated under reduced pressure. The residue was triturated with methanol and filtered to give the title compound as a white solid (18 g).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 18 h
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customThe residue was triturated with methanol
  6. filtrationfiltered

Sources & evidence

ORD record
ord-aa04cc7252424019b3391b1a78f936ff
Source dataset
uspto-grants-2003_12
Patent number
US06670381B2

Reaction notes

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