Triethylamine → 5-Ethoxyindolin-2-one

HRID 2197

Reaction equation

HRID 2197 reaction equation
C[CH2:2][C:3]([O:5]CC)=S.ClCl.[CH2:10]([O:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1)[CH3:11].C(N(CC)CC)C>C(Cl)Cl.O>[CH2:10]([O:12][C:13]1[CH:19]=[C:18]2[C:16](=[CH:15][CH:14]=1)[NH:17][C:3](=[O:5])[CH2:2]2)[CH3:11]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 90764-EthoxyanilineHCID 24526ChlorineHCID 12284386Ethyl methylthioacetate

Product 1

HCID 113558125-Ethoxyindolin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

23.6 g of ethyl methylthioacetate in 60 ml of DCM are added to a solution, cooled to about -70° C., of 12.5 g of chlorine in 400 ml of DCM. After stirring for 5 minutes at the same temperature, a solution of 4-ethoxyaniline (48.3 g) in 120 ml of DCM is added. The mixture is stirred for one hour at about -70° C., 39.3 ml of triethylamine are added and the resulting mixture is allowed to warm up to room temperature. 200 ml of water are added and the organic phase is decanted, dried over magnesium sulfate and evaporated under reduced pressure. The residue is taken up with 500 ml of isopropanol and 20 ml of concentrated hydrochloric acid. The mixture is stirred for about 16 hours at room temperature and filtered and the precipitate is separated off. The filtrate is concentrated under reduced pressure to give the expected product.

Workup

  1. stirringThe mixture is stirred for one hour at about -70° C.
  2. customthe organic phase is decanted
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. stirringThe mixture is stirred for about 16 hours at room temperature
  6. filtrationfiltered
  7. customthe precipitate is separated off
  8. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-137bd4435e364643b101a1a71a0e2096
Source dataset
uspto-grants-1998_03
Patent number
US05728723

Linked notes

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