Triethylamine → HCID 19977165, compound

HRID 865233Notes

Reaction equation

HRID 865233 reaction equation
C(OCl)(C)(C)C.FC(F)(F)[C:9]1[CH:10]=[C:11]([CH:13]=[C:14](C(F)(F)F)[CH:15]=1)[NH2:12].[CH3:22][S:23][CH2:24][C:25](OCC)=[O:26].C(N(CC)CC)C>C(Cl)Cl>[CH3:22][S:23][C:24]1[C:25](=[O:26])[N:12]=[C:11]2[C:10]=1[CH:9]=[CH:15][CH:14]=[CH:13]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9480Benzenamine, 3,5-bis(trifluoromethyl)-HCID 78199Ethyl (methylthio)acetateHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 19977165HCID 19977165, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-65 °C

Procedure

Freshly prepared tBuOCl (2.2 g, 20 mmol) was added dropwise to a stirred cold (-65 ° C.) solution of 3,5-bis-(trifluoromethyl)aniline (4.58 g, 20 mmol) in anhydrous CH2Cl2 (25 mL). After 10 minutes, neat ethyl (methylthio)acetate (2.68 g, 20 mmol) was added and the mixture; stirred at -65° C. for 1 hr. Triethylamine (2.68 g, 20 mmol) was added and then the mixture was allowed to warm to room temperature. The reaction mixture was quenched with water, the organic layer was separated and then rotary evaporated. The oily residue (6.35 g) was dissolved in hexanes and boiled for several hours and then allowed to cool. The precipitated beige solid was filtered and washed with hexanes to afford 3.67 g of pure (methylthio) indolone intermediate.

Workup

  1. temperatureto warm to room temperature
  2. customThe reaction mixture was quenched with water
  3. customthe organic layer was separated
  4. dissolutionThe oily residue (6.35 g) was dissolved in hexanes
  5. waitboiled for several hours
  6. temperatureto cool
  7. filtrationThe precipitated beige solid was filtered
  8. washwashed with hexanes

Sources & evidence

ORD record
ord-070e6eb76c5041ceba7af9fe3d875eea
Source dataset
uspto-grants-1996_10
Patent number
US05565483

Reaction notes

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