Hexane → HCID 178472849, compound

HRID 1074097Notes

Reaction equation

HRID 1074097 reaction equation
[F:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[NH:10]=[C:11](SCC)[C:12]([O:14][CH2:15][CH3:16])=[O:13].CCCCCC>C(Cl)Cl>[NH:10]=[C:11]([NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([F:1])[C:3]=1[CH3:9])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 8058HexaneHCID 2855533-Fluoro-2-methylanilineHCID 13153550HCID 13153550, compound

Product 1

HCID 178472849HCID 178472849, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-fluoro-2-methylaniline (200 mmol, 25 g) in methylene chloride (70 ml) was added a solution of ethyl imino(ethylthio)acetate hydrogentetrafluorobarate (200 mmol) prepared by a method disclosed in Japanese Patent Laid-open Publication No. 56-39092 in methylene chloride (100 ml), and the mixture was thoroughly shaken and allowed to stand at room temperature for 12 hours. At the end of the period, n-hexane (300 ml) was added to the reaction mixture and the mixture was allowed to stand for 2 hours. After removal of a supernatant by decantation, methylene chloride (200 ml) was added to the remaining mixture, which was then neutralized by addition of an aqueous solution of sodium bicarbonate with thorough stirring. From the resulting mixture an organic phase (a solution in methylene chloride) was separated and dried over anhydrous magnesium sulfate overnight. After removal of inorganic materials by filtration, the filtrate was concentrated under reduced pressure to obtain ethyl imino[(3-fluoro-2-methylphenyl)amino]acetate. The product was dissolved in ethanol (80 ml), and to the resulting solution 37% formalin (30 ml) was added and the mixture was thoroughly shaken and allowed to stand overnight. The crystalline product so produced was filtered and recrystallized from ethanol. A white crystalline product (86 mmol, 18 g) was obtained in a yield of 43%.

Workup

  1. customprepared by a method
  2. waitto stand for 2 hours
  3. customAfter removal of a supernatant by decantation, methylene chloride (200 ml)
  4. additionwas added to the remaining mixture, which
  5. additionwas then neutralized by addition of an aqueous solution of sodium bicarbonate with thorough stirring
  6. customFrom the resulting mixture an organic phase (a solution in methylene chloride) was separated
  7. dry with materialdried over anhydrous magnesium sulfate overnight
  8. customAfter removal of inorganic materials
  9. filtrationby filtration
  10. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-77d05ee00f86484693e7164e08a6e823
Source dataset
uspto-grants-1990_11
Patent number
US04973351

Reaction notes

Loading…