Triethylamine → HCID 86691876, compound

HRID 517728Notes

Reaction equation

HRID 517728 reaction equation
C(N(CC)CC)C.[F:8][S:9]([F:20])([F:19])([F:18])([F:17])[C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1.[C:21]([O:24][CH2:25][C:26](Cl)=[O:27])(=[O:23])[CH3:22]>C(Cl)Cl>[C:21]([O:24][CH2:25][C:26](=[O:27])[NH:14][C:13]1[CH:12]=[CH:11][C:10]([S:9]([F:17])([F:18])([F:19])([F:20])[F:8])=[CH:16][CH:15]=1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 27791904-Aminophenylsulphur pentafluoride

Product 1

HCID 86691876HCID 86691876, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (13.9 g, 137 mmol) was added to a stirred solution of 4-(pentafluoro-λ6-sulfanyl)aniline (Commercially available, for example from Apollo Scientific, Stockport, UK, 10.0 g, 45.6 mmol) in DCM (100 mL) at 0° C. and the mixture was stirred for 15 mins. 2-Chloro-2-oxoethyl acetate (7.47 g, 54.7 mmol) was added at 0° C., and the temperature was raised to room temperature with stirring continued for 4 hr. The reaction mixture was diluted with DCM and washed with ice water, saturated aq NaHCO3 solution and brine solution, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give the crude product. This was purified by recrystallisation from ether (500 mL) to give the title compound (8.64 g).

Workup

  1. stirringwith stirring
  2. waitcontinued for 4 hr
  3. washwashed with ice water, saturated aq NaHCO3 solution and brine solution
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product
  7. customThis was purified by recrystallisation from ether (500 mL)

Sources & evidence

ORD record
ord-1666f3aadc2f41178df7192e26944794
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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