Sodium Hydroxide → 3-[(4-chlorophenyl)methyl]-2-(1,1-dimethylethyl)-3,5,6,7-tetrahydro-4H-benzimidazol-4-one

HRID 1946516Notes

Reaction equation

HRID 1946516 reaction equation
[CH3:1][C:2]([C:5]1[NH:9][C:8]2[CH2:10][CH2:11][CH2:12][C:13](=[O:14])[C:7]=2[N:6]=1)([CH3:4])[CH3:3].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:6]2[C:7]3[C:13](=[O:14])[CH2:12][CH2:11][CH2:10][C:8]=3[N:9]=[C:5]2[C:2]([CH3:1])([CH3:3])[CH3:4])=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 584602242-(1,1-dimethylethyl)-1,5,6,7-tetrahydro-4H-benzimidazol-4-one

Product 1

HCID 584602033-[(4-chlorophenyl)methyl]-2-(1,1-dimethylethyl)-3,5,6,7-tetrahydro-4H-benzimidazol-4-one

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

To a stirred suspension of Intermediate 52 (325 mg), 1-(bromomethyl)-4-chlorobenzene (417 mg) and tetrabutylammonium bromide (272 mg) in toluene (8 mL) at ambient temperature was added aqueous sodium hydroxide 20% wt (3.25 mL). The reaction was stirred at ambient temperature for 2.5 hr. The reaction was quenched with water (20 mL) and extracted with ethyl acetate (2×20 mL). The combined organics were dried (hydrophobic frit) and concentrated in vacuo. The sample was loaded in dichloromethane and purified on silica using a 0-100% ethyl acetate-cyclohexane gradient. The appropriate fractions were combined and evaporated in vacuo to give the title compound. (126 mg). LC/MS MH+ 317, Rt 2.10 mins (5 min run).

Workup

  1. customThe reaction was quenched with water (20 mL)
  2. extractionextracted with ethyl acetate (2×20 mL)
  3. customThe combined organics were dried (hydrophobic frit)
  4. concentrationconcentrated in vacuo
  5. custompurified on silica using a 0-100% ethyl acetate-cyclohexane gradient
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-0762ed5ac5684e9fb491b281f65eb995
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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