Ammonia → 6-chloro-N-methyl-N-phenyl-[1,3,5]triazine-2,4-diamine

HRID 341473Notes

Reaction equation

HRID 341473 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([N:9]([CH3:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1.[NH3:17]>C1COCC1>[Cl:8][C:6]1[N:5]=[C:4]([N:9]([CH3:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=[C:2]([NH2:17])[N:7]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 198964,6-dichloro-N-methyl-N-phenyl-1,3,5-triazin-2-amine2×

Product 1

HCID 807666266-chloro-N-methyl-N-phenyl-[1,3,5]triazine-2,4-diamineYield 110%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of (4,6-dichloro-[1,3,5]triazin-2-yl)-methyl-phenyl-amine (Intermediate 42, 2.7 g, 10.58 mmol) in THF (45 ml) was added a solution of conc. aqueous ammonia (3 ml, 52.91 mmol). The reaction was allowed to stir at room temperature for 1 h, the reaction was then diluted with THF (50 ml), treated with conc. aqueous ammonia (1 ml, 17.64 mmol) and stirred for 18 h. The reaction was concentrated under vacuum and taken up in DCM (150 ml); the solution was then extracted with 2M aq. HCl (2×50 mL), and saturated brine (20 mL) and dried further over anhydrous sodium sulfate. The organic phase was evaporated to dryness to furnish the product as an off white solid (2.743 g, 110%). Method B HPLC-MS: MH+ requires m/z=236. Found: m/z=236, Rt=1.76 min (88%). 1H NMR (500 MHz, CDCl3) δ ppm 7.09-7.44 (5H, m), 5.21-5.65 (2H, m), 3.40 (3H, s).

Workup

  1. stirringstirred for 18 h
  2. concentrationThe reaction was concentrated under vacuum
  3. extractionthe solution was then extracted with 2M aq. HCl (2×50 mL), and saturated brine (20 mL)
  4. dry with materialdried further over anhydrous sodium sulfate
  5. customThe organic phase was evaporated to dryness

Sources & evidence

ORD record
ord-0e57402353de4b5abd7e9d122aec1bfd
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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