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

HRID 1622491Notes

Reaction equation

HRID 1622491 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

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]+

Workup

  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

Sources & evidence

ORD record
ord-3a9041637b884265a4d3e4928d1147dc
Source dataset
uspto-grants-2014_07
Patent number
US08778937B2

Reaction notes

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