Hydrochloric Acid → HCID 57507185, compound

HRID 1931189Notes

Reaction equation

HRID 1931189 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.[N:13]1[C:20]([Cl:21])=[N:19][C:17](Cl)=[N:16][C:14]=1[Cl:15].C(=O)([O-])[O-].[K+].[K+].Cl>O1CCCC1.C(OCC)(=O)C>[Cl:15][C:14]1[N:13]=[C:20]([Cl:21])[N:19]=[C:17]([NH:8][C:7]2[CH:9]=[CH:10][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:5][CH:6]=2)[N:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7954Cyanuric chlorideHCID 11430Potassium CarbonateHCID 6008484-(Trifluoromethoxy)aniline

Product 1

HCID 57507185HCID 57507185, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of 4-trifluoromethoxyaniline (XII) (14.66 mL, 108 mmol) in dry tetrahydrofuran (THF; 120 mL) was added, dropwise, to a cold (0-5° C.) stirred suspension of cyanuric chloride (II) (20.0 g, 108 mmol) and potassium carbonate (15 g, 108 mmol) in dry THF (400 mL). The reaction mixture was stirred for 3 h while slowly warming to ambient temperature. After stirring for 14 h at ambient temperature, the reaction mixture was diluted with ethyl acetate (400 mL) and then acidified with 1 N aqueous hydrochloric acid. The organic phase was separated, rinsed successively with water, saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum on a rotary evaporator. The residue, an off white solid, was recrystallized from hot hexanes to afford (4,6-dichloro-1,3,5-triazin-2-yl)-(4-trifluoromethoxyphenyl)-amine (XIII) (35.1 g, 99% yield): m.p. 119-122° C.; 1H NMR (CDCl3) δ 7.62 (d, J=3.3 Hz, 2H), 7.58 (d, J=2.2 Hz, 2H); ESI/MS 325 (M+H), 323 (M−H); Anal. Calcd. For C10H5Cl2F3N4O: C, 36.95; H, 1.55; N, 17.53. Found: C, 36.80; H, 1.53; N, 16.98.

Workup

  1. stirringThe reaction mixture was stirred for 3 h
  2. temperaturewhile slowly warming to ambient temperature
  3. stirringAfter stirring for 14 h at ambient temperature
  4. customThe organic phase was separated
  5. washrinsed successively with water, saturated aqueous sodium bicarbonate and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum on a rotary evaporator
  9. customThe residue, an off white solid, was recrystallized from hot hexanes

Sources & evidence

ORD record
ord-8eeaa6dad9214befa09425f230e9ec06
Source dataset
uspto-grants-2012_05
Patent number
US08188273B2

Reaction notes

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