Cyanuric chloride → 4,6-dichloro-N-[(2R)-2-phenylpropyl]-1,3,5-triazin-2-amine

HRID 1671759Notes

Reaction equation

HRID 1671759 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[CH3:10][C@H:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:12][NH2:13].[OH-].[Na+]>CC#N.O>[Cl:9][C:8]1[N:1]=[C:2]([Cl:3])[N:4]=[C:5]([NH:13][CH2:12][C@@H:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:10])[N:7]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 14798Sodium HydroxideHCID 1547949(R)-(+)-beta-Methylphenethylamine

Product 1

HCID 866443924,6-dichloro-N-[(2R)-2-phenylpropyl]-1,3,5-triazin-2-amine

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A mixture of cyanuric chloride (75 mg, 0.407 mmol, 1 equivalent) in CH3CN/H2O (1/1, 5 ml) was cooled to 0° C. (R)-(+)-beta-methylphenethylamine (55 mg, 0.407 mmol, 1 equivalent) was added, followed by 1N NaOH (0.366 ml). LCMS analysis showed the complete consumption of the 2,4,6-trichloro-1,3,5-triazine. The crude product was used in the next step. MS (ES+): m/e 283.06 [M+H]+.

Workup

  1. additionwas added
  2. customthe complete consumption of the 2,4,6-trichloro-1,3,5-triazine

Sources & evidence

ORD record
ord-3d80e7034fff4ee7a1387ffc13725a5d
Source dataset
uspto-grants-2011_08
Patent number
US07994317B2

Reaction notes

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