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

HRID 1386925
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1386925
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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.

Quellen und Nachweise

ORD-Eintrag
ord-87fa38c32a1b4ab399113e4766c7af16
Quelldatensatz
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06265426B1

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