Dimethylcarbamoyl Chloride → HCID 86710036, compound

HRID 1468266Notes

Reaction equation

HRID 1468266 reaction equation
[CH:1]1([O:7][CH2:8][C:9]2[N:13]3[CH:14]=[CH:15][C:16]([SH:18])=[CH:17][C:12]3=[N:11][C:10]=2[CH:19]([CH3:21])[CH3:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:29][N:30]([CH3:34])[C:31](Cl)=[O:32].C(=O)([O-])O.[Na+]>ClCCCl>[CH3:29][N:30]([CH3:34])[C:31](=[O:32])[S:18][C:16]1[CH:15]=[CH:14][N:13]2[C:9]([CH2:8][O:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[C:10]([CH:19]([CH3:21])[CH3:20])[N:11]=[C:12]2[CH:17]=1

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 178439972HCID 178439972, compound

Product 1

HCID 86710036HCID 86710036, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3-Cyclohexyloxymethyl-2-isopropylimidazo[1,2-a]pyridine-7-thiol (210 mg, 0.691 mmol) obtained in step 1 was dissolved in 1,2-dichloroethane (2.0 mL). Under ice-cooled condition, triethylamine (0.140 mL, 1.00 mmol) and dimethylcarbamoyl chloride (0.0770 mL, 0.834 mmol) were added, and the mixture was stirred at room temperature for 30 minutes. After adding a saturated sodium hydrogen carbonate aqueous solution to the reaction mixture, the reaction mixture was filtered through a Presep (registered trademark; diatomaceous earth, granular type M, 4.5 g/25 mL). The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30) to give S-3-(cyclohexyloxymethyl)-2-isopropylimidazo[1,2-a]pyridin-7-yl dimethylthiocarbamate (121 mg, yield 47%).

Workup

  1. additionwere added
  2. filtrationthe reaction mixture was filtered through a Presep (registered trademark; diatomaceous earth, granular type M, 4.5 g/25 mL)
  3. customThe solvent was then evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30)

Sources & evidence

ORD record
ord-240e097209b3475aabe862ac99c59ddb
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

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