Potassium Carbonate → HCID 22063952, compound

HRID 1828182Notes

Reaction equation

HRID 1828182 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2[CH:13]=[CH:14][C:15]([CH:17]=[O:18])=[CH:16][C:11]=2[N:10]([CH3:19])[C:9]1=[O:20].C1(C)C=CC(S([CH:30]([N+:38]#[C-:39])[C:31]2[CH:32]=[C:33]([CH3:37])[CH:34]=[CH:35][CH:36]=2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]3[O:18][CH:39]=[N:38][C:30]=3[C:31]3[CH:32]=[C:33]([CH3:37])[CH:34]=[CH:35][CH:36]=3)=[CH:16][C:11]=2[N:10]([CH3:19])[C:9]1=[O:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 220638451-[Isocyano(4-methylbenzene-1-sulfonyl)methyl]-3-methylbenzeneHCID 22063864HCID 22063864, compound

Product 1

HCID 22063952HCID 22063952, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A slurry of 1-(2-chloro-phenyl)-3-methyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carbaldehyde (prepared as described previously, 100 mg, 0.35 mmol), [(toluene-4-sulfonyl)-m-tolyl-methyl]-isonitrile (prepared as described previously, 110 mg, 0.38 mmol) and potassium carbonate (53.1 mg, 0.38 mmol) in DMF was heated to 60° C. overnight. The reaction mixture was cooled to room temperature and quenched with water. The resulting aqueous solution was extracted with ethyl acetate and the combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford a brown oil. Purification by HPLC (30–80% acetonitrile/water gradient) afforded 40 mg of the title compound. MS (M+1)=416.3

Workup

  1. customquenched with water
  2. extractionThe resulting aqueous solution was extracted with ethyl acetate
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto afford a brown oil
  7. customPurification by HPLC (30–80% acetonitrile/water gradient)

Sources & evidence

ORD record
ord-a40842c0dd22468194d8e6cbacde037c
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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