Butyryl chloride → HCID 178454438, compound

HRID 1886939Notes

Reaction equation

HRID 1886939 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][C:14]([NH2:16])=[CH:15][C:9]=3[N:8]=2)=[CH:3][CH:2]=1.[C:18](Cl)(=[O:22])[CH2:19][CH2:20][CH3:21].C(OCC)(=O)C>N1C=CC=CC=1>[C:1]1([CH3:17])[CH:2]=[CH:3][C:4]([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][C:14]([NH:16][C:18](=[O:22])[CH2:19][CH2:20][CH3:21])=[CH:15][C:9]=3[N:8]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8855Butyryl chlorideHCID 8857Ethyl AcetateHCID 178423931HCID 178423931, compound

Product 1

HCID 178454438HCID 178454438, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-p-tolyl-1H-benzo[d]imidazol-5-amine (150 mg, 0.67 mmol) in pyridine (10 mL) at room temperature was added butyryl chloride (77 μL, 0.74 mmol). The resulting mixture was stirred at room temperature for 16 h. Ethyl acetate was added and the organic layer was washed twice with saturated aqueous copper sulfate, followed by sodium bicarbonate and brine. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting with ethyl acetate/hexanes 50:50 v/v to afford 56 mg (28%) of the title compound (LCMS RT=6.96 min, MH+ 294.0)

Workup

  1. washthe organic layer was washed twice with saturated aqueous copper sulfate
  2. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  3. customevaporated
  4. customThe resulting solid was purified by column chromatography
  5. washeluting with ethyl acetate/hexanes 50:50 v/v

Sources & evidence

ORD record
ord-e2b1c31d8041444dbd7c596907d11a06
Source dataset
uspto-grants-2013_08
Patent number
US08501713B2

Reaction notes

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