Dimethylcarbamoyl Chloride → HCID 86689847, compound

HRID 2409032Notes

Reaction equation

HRID 2409032 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:11]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:10]=[CH:9][C:5]2=[N+:6]([O-])[CH:7]=1.[CH3:22][N:23](C)C(Cl)=O.C[Si](C#N)(C)C>ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[N:11]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:10]=[CH:9][C:5]2=[N:6][C:7]=1[C:22]#[N:23]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 86689846HCID 86689846, compound

Product 1

HCID 86689847HCID 86689847, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridine-4-oxide (8.75 g, 27.12 mmol) in 1,2-dichloroethane (250 mL) was added dimethylcarbamic chloride (4.37 g, 40.66 mmol) and trimethylsilyl cyanide (4.03 g, 40.66 mmol) successively. The mixture was stirred under nitrogen at 80° C. overnight. The reaction mixture was quenched by adding sat'd. aq. NaHCO3 solution. The organic layer was washed with water (50 mL×3), dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with petroleum ether EtOAc (8:1) to afford 4.8 g (53%) of 6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile as a white solid. MS (ESI): m/z=332.0 [M+1]+.

Workup

  1. customThe reaction mixture was quenched
  2. additionby adding sat'd
  3. washThe organic layer was washed with water (50 mL×3)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by SiO2 chromatography
  8. washeluting with petroleum ether EtOAc (8:1)

Sources & evidence

ORD record
ord-383aba9c03214edb985260c3e5fc3714
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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