Hydrochloric Acid → alpha-(Bromomethyl)-4-(1H-imidazol-1-yl)benzenemethanol

HRID 232310

반응식

HRID 232310 반응식
Br.[Br:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:8][CH:7]=1)=[O:5].C([BH3-])#N.[Na+].CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C.Cl>CO>[Br:2][CH2:3][CH:4]([C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:10][CH:11]=1)[OH:5]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 5003444Sodium cyanoborohydrideHCID 200313102-Bromo-1-[4-(1H-imidazol-1-yl)phenyl]ethanone hydrobromide

생성물 1

HCID 20031362alpha-(Bromomethyl)-4-(1H-imidazol-1-yl)benzenemethanol

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

Stir a mixture of 2-bromo-1-[4-(1H-imidazol-1-yl)-phenyl]ethanone hydrobromide (15.45 g, 44.6 mmol) and sodium cyanoborohydride (5.61 g, 89.3 mmol) in methanol (250 mL). Add a crystal of methyl orange and adjust the pH to 3.0 with 1.35M hydrochloric acid in methanol. Maintain the pH at 3.0 for about 2 hr. Treat the resulting solution with decolorizing carbon and filter through celite. Concentrate the filtrate and add water (200 mL) and methylene chloride (100 mL) to the residue. Adjust the pH to 7.5 with 2N NaOH solution. Separate the layers and extract the aqueous layer with methylene chloride (100 mL) and combine, dry over Na2SO4, filter and concentrate in vacuo. Add ethyl acetate to the residue to afford crystals of the title compound.

후처리

  1. temperatureMaintain the pH at 3.0 for about 2 hr
  2. additionTreat the resulting solution with decolorizing carbon
  3. filtrationfilter through celite
  4. concentrationConcentrate the filtrate
  5. additionadd water (200 mL) and methylene chloride (100 mL) to the residue
  6. customSeparate the layers
  7. extractionextract the aqueous layer with methylene chloride (100 mL)
  8. dry with materialdry over Na2SO4
  9. filtrationfilter
  10. concentrationconcentrate in vacuo

출처 및 근거

ORD 기록
ord-4f7dcaa715774f9f894b866d61c454e1
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04851526

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