Hydrochloric Acid → 4-[5-(3-Dimethylaminomethyl-phenyl)-2H-[1,2,4]triazol-3-yl]-phenol hydrochloride salt

HRID 1386925Notes

Reaction equation

HRID 1386925 reaction equation
[ClH:1].C[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=3)[CH2:18][N:19]([CH3:21])[CH3:20])[N:11]=2)=[CH:6][CH:5]=1.B(Br)(Br)Br.C([O-])([O-])=O.[Na+].[Na+].Cl>C(Cl)Cl.CO>[ClH:1].[CH3:21][N:19]([CH2:18][C:17]1[CH:16]=[C:15]([C:12]2[N:11]=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([OH:3])=[CH:9][CH:8]=3)[NH:14][N:13]=2)[CH:24]=[CH:23][CH:22]=1)[CH3:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 21180376{3-[5-(4-methoxy-phenyl)-1H-[1,2,4]triazol-3-yl]-benzyl}-dimethylamine hydrochloride

Product 1

HCID 1357941164-[5-(3-Dimethylaminomethyl-phenyl)-2H-[1,2,4]triazol-3-yl]-phenol hydrochloride saltYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of {3-[5-(4-methoxy-phenyl)-1H-[1,2,4]triazol-3-yl]-benzyl}-dimethylamine hydrochloride (1:1) (100 mg, 0.29 mmol) in CH2Cl2 (5 ml) at −78° C. was treated with boron tribromide (1M CH2Cl2 1.5 ml, 1.5 mmol, 5.2 eq.). Over 16 hrs. the temperature was raised gradually to r.t. After addition of methanol (1 ml) and saturated Na2CO3 (10 ml) the pH was adjusted to 9 with 2N HCl. After extraction with CH2Cl2, then EtOAc, the combined extracts were dried with Na2SO4 and the solvent evaporated. The residue was dissolved in EtOH, 1.45M HCl/EtOH added (0.17 ml, 1.1 eq.) and stirred for 30 min. then evaporated to dryness and the product obtained was dried under high vacuum at 20° C., affording the title compound (70 mg, 73% yield) as a light yellow solid. MS: m/e=295.3 (M+H+).

Workup

  1. extractionAfter extraction with CH2Cl2
  2. dry with materialEtOAc, the combined extracts were dried with Na2SO4
  3. customthe solvent evaporated
  4. dissolutionThe residue was dissolved in EtOH
  5. addition1.45M HCl/EtOH added (0.17 ml, 1.1 eq.)
  6. customthen evaporated to dryness
  7. customthe product obtained
  8. customwas dried under high vacuum at 20° C.

Sources & evidence

ORD record
ord-87fa38c32a1b4ab399113e4766c7af16
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

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