Hydrochloric Acid → 4-bromo-2-isopropyl-1-(2-methyl-3-(trifluoromethyl)benzyl)-1H-benzo[d]imidazol-6-amine

HRID 1622491노트

반응식

HRID 1622491 반응식
[Br:1][C:2]1[C:10]2[N:9]=[C:8]([CH:11]([CH3:13])[CH3:12])[N:7]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[C:16]=3[CH3:25])[C:6]=2[CH:5]=[C:4]([N+:26]([O-])=O)[CH:3]=1.O.O.[Sn](Cl)Cl.Cl.C(=O)([O-])[O-].[Na+].[Na+]>CO>[Br:1][C:2]1[C:10]2[N:9]=[C:8]([CH:11]([CH3:13])[CH3:12])[N:7]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:23])([F:22])[F:24])[C:16]=3[CH3:25])[C:6]=2[CH:5]=[C:4]([NH2:26])[CH:3]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 61436Stannous chloride dihydrateHCID 866878474-bromo-2-isopropyl-1-(2-methyl-3-(trifluoromethyl)benzyl)-6-nitro-1H-benzo[d]imidazole

생성물 1

HCID 866878484-bromo-2-isopropyl-1-(2-methyl-3-(trifluoromethyl)benzyl)-1H-benzo[d]imidazol-6-amine수율 70.9%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

To a 250 mL round-bottom flask containing MeOH (100 mL) was added crude 4-bromo-2-isopropyl-1-(2-methyl-3-(trifluoromethyl)benzyl)-6-nitro-1H-benzo[d]imidazole (7.1 g, 15.56 mmol), tin(II) chloride dihydrate (10.53 g, 46.7 mmol) and hydrochloric acid (6.48 mL, 78 mmol). The resultant suspension was heated to 60° C. and monitored by LC/MS. By LC/MS the reaction was complete in 30 minutes. After the reaction had cooled to rt, the majority of the MeOH was removed in-vacuo and sodium carbonate (150 mL, 150 mmol) was added slowly to adjust the pH to about 10 and the mixture was extracted with Et2O (150 mL) and the organic was washed with H2O and brine and dried over MgSO4 and filtered. The solvent was removed in-vacuo leaving the desired product (4.7 g, 11.03 mmol, 70.9% yield) as crude brown solid that by LC/MS was sufficiently pure to use in the next step. MS (ES+) m/e: 425.1, 426.0 [M+H]+

후처리

  1. additionwas added slowly
  2. extractionthe mixture was extracted with Et2O (150 mL)
  3. washthe organic was washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed in-vacuo

출처 및 근거

ORD 기록
ord-3a9041637b884265a4d3e4928d1147dc
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778937B2

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