Dimethyl Sulfide → HCID 19363473, compound

HRID 850471Notes

Reaction equation

HRID 850471 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:5]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:6].[CH3:18][S:19][CH3:20].ClN1C(=O)CCC1=O.C(N(CC)CC)C>[Cl-].[Na+].O.C(Cl)Cl>[NH2:1][C:2]1[C:3]([CH2:18][S:19][CH3:20])=[C:4]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:5]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:6]

Participants

7

Reactant 4

HCID 1068Dimethyl SulfideHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 19363226HCID 19363226, compound

Product 1

HCID 19363473HCID 19363473, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
-30 °C

Procedure

Pentyl 3-amino-4-methoxybenzoate (0.744 g, 4.45 mmol), methylene chloride (15 ml) and dimethylsulfide (0.33 ml, 4.50 mmol) were mixed, and after cooling to -30° C., N-chlorosuccinimide (601 mg, 4.5 mmol) was added to this solution. After sti ring for 1 hour, triethylamine (0.627 ml, 4.5 mmol) was added, and the mixture was refluxed under heating for 0.5 hour. Saturated brine (0.5 ml) was added to stop the reaction, the reaction mixture was concentrated under reduced pressure. The obtained residue was purified by column chromatography (hemne/ethyl acetate=4/1) to give pentyl 3-amino-4-methoxy-2-methylthiomethylbenzoate (0.83 g, 82%) as a brown oil.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 0.5 hour
  3. customthe reaction
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customThe obtained residue was purified by column chromatography (hemne/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-a35934a4204c42f2ae97078cd35df2df
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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