Hydrochloric Acid → HCID 66697360, compound

HRID 2386803Notes

Reaction equation

HRID 2386803 reaction equation
C[C:2]([CH3:5])([O-])[CH3:3].[K+].[CH3:7][O:8][C:9]([C:11]1[CH:20]=[CH:19][C:14]2[NH:15][C:16](=[O:18])[NH:17][C:13]=2[CH:12]=1)=[O:10].[CH2:21](Br)[CH:22]=[CH2:23].Cl>CC(N(C)C)=O>[CH3:7][O:8][C:9]([C:11]1[CH:20]=[CH:19][C:14]2[N:15]([CH2:23][CH:22]=[CH2:21])[C:16](=[O:18])[N:17]([CH2:3][CH:2]=[CH2:5])[C:13]=2[CH:12]=1)=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 10352553methyl 2-oxo-2,3-dihydro-1H-1,3-benzodiazole-5-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 66697360HCID 66697360, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Potassium tert-butoxide (2.57 g) was added to a solution of 2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methyl ester (2 g) in DMA (30 ml). Allyl bromide (2 ml) was added, and the mixture was stirred for 2 h at room temperature. The mixture was acidified with 2N aqueous HCl and then extracted with EtOAc. The combined organic layers were dried over Na2SO4 and then concentrated to an oil. The residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:2) to give the title compound (2.2 g) as a yellow oil. MS (m/e)=273.2 [M+H+].

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated to an oil
  4. customThe residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:2)

Sources & evidence

ORD record
ord-ddb53d4206e840579ffa2248f3d0919a
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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