Dimethyl Sulfide → HCID 22175707, compound

HRID 1797607Notes

Reaction equation

HRID 1797607 reaction equation
[NH2:1][CH2:2][C:3]1[N:4]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:5](=[O:20])[C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][C:9](Br)=[CH:8][CH:7]=2.C[S-].[Na+].[CH3:28][S:29]C>>[NH2:1][CH2:2][C:3]1[N:4]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:5](=[O:20])[C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][C:9]([S:29][CH3:28])=[CH:8][CH:7]=2

Participants

4

Reactant 3

HCID 1068Dimethyl SulfideHCID 4378561Sodium methanethiolate2×HCID 22175497HCID 22175497, compound

Product 1

HCID 22175707HCID 22175707, compoundYield 88%

Conditions

Temperature
70 °C

Procedure

A mixture of 3-(aminomethyl)-6-bromo-2-isobutyl-4-phenyl-1(2H)-isoquinolinone (0.19 g, 0.50 mmol), sodium thiomethoxide (0.043 g, 0.60 mmol) and dimethylsulfide (2 mL) was stirred at 70° C. for 2 h. To the reaction mixture was added another sodium thiomethoxide (0.043 g, 0.60 mmol), and the resulting mixture was stirred at 70° C. for 2 h. The reaction mixture was partitioned between water (100 mL) and ethyl acetate (25 mL) and the aqueous layer was extracted with ethyl acetate (25 mL). The extracts were combined and washed once each with saturated aqueous sodium hydrogencarbonate (25 mL) and saturated brine (25 mL), dried over anhydrous magnesium sulfate (12 g) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:5 (v/v)) to give 3-(aminomethyl)-2-isobutyl-6-(methylsulfanyl)-4-phenyl-1(2H)-isoquinolinone (0.16 g, 88%) as an oil.

Workup

  1. stirringthe resulting mixture was stirred at 70° C. for 2 h
  2. customThe reaction mixture was partitioned between water (100 mL) and ethyl acetate (25 mL)
  3. extractionthe aqueous layer was extracted with ethyl acetate (25 mL)
  4. washwashed once each with saturated aqueous sodium hydrogencarbonate (25 mL) and saturated brine (25 mL)
  5. dry with materialdried over anhydrous magnesium sulfate (12 g)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:5 (v/v))

Sources & evidence

ORD record
ord-78634e3bc1284c85b590377a10a6f08d
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

Loading…