Acetone → HCID 58503687, compound

HRID 623811Notes

Reaction equation

HRID 623811 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[S:10])[NH2:9])[CH:5]=[C:4]([O:11][CH3:12])[N:3]=1.CI.[CH3:15]C(C)=O.CCCCCC>C(OCC)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([S:10][CH3:15])=[NH:9])[CH:5]=[C:4]([O:11][CH3:12])[N:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 8058HexaneHCID 58503835HCID 58503835, compound

Product 1

HCID 58503687HCID 58503687, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a 100-mL, 3N round-bottomed flask equipped with Thermometer pocket fitted with water condenser, nitrogen inlet and a rubber septum, 2-chloro-6-methoxypyridine-4-carbothioamide (0.58 g, 1.0 eq.), methyl iodide (0.89 mL, 5.0 eq.) was dissolved in diethyl ether (60 mL) resulting reaction mixture was stir at RT. The progress of the reaction was followed by TLC analysis on silica gel with 20% acetone: hexane as mobile phase which shows that starting material was consumed after 15 h. Precipitate was observed that was collected by filtration on Buchner funnel. Solid was separated and compound was collected by filtration on a Buchner funnel and washed with hexane (100 mL); Yield: 0.257 g (41.44%); LCMS (%): 27.07% [M+H]+ 217.92 RT: 4.216 min. (Crude).

Workup

  1. customIn a 100-mL, 3N round-bottomed flask equipped with Thermometer pocket
  2. customfitted with water condenser, nitrogen inlet
  3. customresulting
  4. customreaction mixture
  5. customwas consumed after 15 h
  6. filtrationthat was collected by filtration on Buchner funnel
  7. customSolid was separated
  8. filtrationcompound was collected by filtration on a Buchner funnel
  9. washwashed with hexane (100 mL)

Sources & evidence

ORD record
ord-c49678cea93846698fe923589735b6af
Source dataset
uspto-grants-2016_04
Patent number
US09303000B2

Reaction notes

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