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

HRID 1386925

反応式

HRID 1386925 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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+).

後処理

  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.

出典と根拠

ORDレコード
ord-87fa38c32a1b4ab399113e4766c7af16
出典データセット
uspto-grants-2001_07
特許番号
US06265426B1

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