Cyanuric chloride → HCID 58964567, compound

HRID 1160104Notes

Reaction equation

HRID 1160104 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[OH:10][CH2:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=1)=[O:13].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:9][C:8]1[N:1]=[C:2]([Cl:3])[N:4]=[C:5]([O:10][CH2:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:22])([F:23])[F:24])[CH:16]=2)=[O:13])[N:7]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 81531DiisopropylethylamineHCID 24284802HCID 24284802, compound

Product 1

HCID 58964567HCID 58964567, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 200 mL recovery flask was added cyanuric chloride (504 mg, 2.73 mmol, 1.0 eq.) and CH2Cl2 (50 mL). The solution was cooled to 0° C. In a separate flask, a solution of 2-hydroxy-N-(3-trifluoromethyl-phenyl)-acetamide (599 mg, 2.73 mmol, 1.0 eq.) and i-Pr2NEt (524 μL, 2.00 mmol, 1.1 eq.) in 10 mL was prepared and then slowly added to the reaction flask. The reaction was stirred for 2 h while warming to room temperature. The reaction was quenched with H2O (50 mL). The organic phase washed with brine (1×50 mL). The combined aqueous phases were extracted with CH2Cl2 (2×25 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated to give an off-white solid. The crude material was purified via flash chromatography (1:4 EtOAc/Hexanes) to give 2-(4,6-dichloro-[1,3,5]triazin-2-yloxy)-N-(3-trifluoromethyl-phenyl)-acetamide as a white solid (600 mg, 60%). LC/MSD (HP Series 1100 MSD) Expected MW: 365.99, Observed M+H: 367.0, Retention time: 1.59. 1H-NMR, DMSO-d6, Varian 400 MHz δ 11.19 (s, 1H), 10.63 (s, 1H), 8.08 (s, 1H), 7.75 (d, 1H), 7.59 (t, 1H), 7.44 (d, 1H), 4.99 (s, 2H) ppm.

Workup

  1. additionslowly added to the reaction flask
  2. temperaturewhile warming to room temperature
  3. customThe reaction was quenched with H2O (50 mL)
  4. washThe organic phase washed with brine (1×50 mL)
  5. extractionThe combined aqueous phases were extracted with CH2Cl2 (2×25 mL)
  6. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give an off-white solid
  10. customThe crude material was purified via flash chromatography (1:4 EtOAc/Hexanes)

Sources & evidence

ORD record
ord-3a42fbc7c6b1413cb3fef7a0a2e1dfc2
Source dataset
uspto-grants-2010_10
Patent number
US07816353B2

Reaction notes

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