Sodium Hydroxide → HCID 10970289, compound

HRID 650040Notes

Reaction equation

HRID 650040 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:24]C)=[C:6]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)=[N:11][N:10]=[C:9]2[NH2:23])[CH:7]=1.B(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:24])=[C:6]([N:8]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:17][CH:18]=3)=[N:11][N:10]=[C:9]2[NH2:23])[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 10926720HCID 10926720, compound

Product 1

HCID 10970289HCID 10970289, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-(5-Chloro-2-methoxyphenyl)-5-[4-(trifluoromethyl)-phenyl]-4H-1,2,4-triazol-3-amine (1.5 g, 4.1 mmol) was taken up in methylene chloride (forms suspension), cooled to 0° C. under N2, and from 3 to 6 eq. boron tribromide (25 ml, 1.0M in CH2Cl2) added. The reaction was stirred at 24° C. for 18 h, and 1N sodium hydroxide (80 ml) was added and the solvent was removed by rotary evaporation and the residue was taken up in ethyl acetate and enough THF added to complete dissolution. After being washed with 0.1N HCl solution and brine the solution was dried over MgSO4. Chromatography, elution 1% AcOH/5% methanol in dichloromethane gave 795 mg (55%). mp 147-155° C. H. Res. MS calcd. for C15H10ClF3N4O: 355.0574; Found: 355.0566; Dev: 2.3 ppm.

Workup

  1. customthe solvent was removed by rotary evaporation
  2. additionenough THF added to complete dissolution
  3. washAfter being washed with 0.1N HCl solution and brine the solution
  4. dry with materialwas dried over MgSO4
  5. washChromatography, elution 1% AcOH/5% methanol in dichloromethane
  6. customgave 795 mg (55%)

Sources & evidence

ORD record
ord-a783d4a659cb4d63b74038ab1c96db55
Source dataset
uspto-grants-2001_08
Patent number
US06271249B1

Reaction notes

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