Ammonia → HCID 58513608, compound

HRID 1817888Notes

Reaction equation

HRID 1817888 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:13])[C:5]([NH:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)=[CH:6][CH:7]=1.[C:14]([CH2:18][C:19](Cl)=[O:20])([CH3:17])([CH3:16])[CH3:15].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.N>C(OCC)(=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([CH2:9][CH:10]3[CH2:12][CH2:11]3)[C:19]([CH2:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[N:13][C:4]=2[CH:3]=1.[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)=[C:4]([NH:13][C:19](=[O:20])[CH2:18][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:3]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 815143,3-Dimethylbutanoyl chlorideHCID 521998p-Toluenesulfonic acid monohydrateHCID 43115327HCID 43115327, compound

Product 2

HCID 58513608HCID 58513608, compoundYield 49%HCID 59253284HCID 59253284, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromo-N1-(cyclopropylmethyl)benzene-1,2-diamine (Step B, 1.48 g, 6.15 mmol) in ethyl acetate (30 mL) was added tert-butylacetyl chloride (940 μL, 6.77 mmol) at room temperature. After stirring for 1 h, p-toluenesulfonic acid monohydrate (1.29 g, 6.77 mmol) was added and the mixture was stirred under reflux for 9 h. Water (20 mL) and aqueous ammonia (10 mL) were added and the mixture was extracted with ethyl acetate (30 mL×2) and washed with brine (10 mL). The organic extracts were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1 as eluent) to give 5-bromo-1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazole (965 mg, 49%) as a brown oil and N-{5-Bromo-2-[(cyclopropylmethyl)amino]phenyl}-3,3-dimethylbutanamide (761 mg, 36%) as a white solid.

Workup

  1. stirringthe mixture was stirred
  2. temperatureunder reflux for 9 h
  3. extractionthe mixture was extracted with ethyl acetate (30 mL×2)
  4. washwashed with brine (10 mL)
  5. dry with materialThe organic extracts were dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1 as eluent)

Sources & evidence

ORD record
ord-2085373b5e5a46528ad1c3465b719be4
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

Loading…