Acetyl chloride → 1-[2-(3-Ethyl-5-methyl-1,2-oxazol-4-yl)-1H-indol-3-yl]ethan-1-one

HRID 1380574Notes

Reaction equation

HRID 1380574 reaction equation
[CH2:1]([C:3]1[C:7]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:6]([CH3:17])[O:5][N:4]=1)[CH3:2].[C:18](Cl)(=[O:20])[CH3:19]>C(Cl)Cl.FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH2:1]([C:3]1[C:7]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:6]([CH3:17])[O:5][N:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 130386862-(3-Ethyl-5-methyl-1,2-oxazol-4-yl)-1H-indole

Product 1

HCID 128514531-[2-(3-Ethyl-5-methyl-1,2-oxazol-4-yl)-1H-indol-3-yl]ethan-1-one

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

In the alternate procedure, 41.8 grams (0.163 moles) of silver triflouromethanesulfonate is added portionwise to a solution of 33.5 grams (0.148 mole) of 2-(3-ethyl-5-methyl-4-isoxazolyl)-indole in 450 milliliters of methylene chloride. The resulting suspension is then treated by dropwise addition with 12.8 grams (0.163 moles) of acetyl chloride in 50 milliliters of methylene chloride. The temperature rises to 35° C. during the addition. After the addition is complete, the mixture is stirred at room temperature for 4 hours and then filtered. The filtrate is washed with 150 milliliters of 2N sodium hydroxide, water and 2N sodium hydroxide, then dried over anhydrous magnesium sulfate and finally evaporated in vacuo to yield an oil. The oil is crystallized from ether to give 2-(3-ethyl-5-methyl-4-isoxazolyl)-3-acetyl indole, m.p. 170°-173° C.

Workup

  1. additionThe temperature rises to 35° C. during the addition
  2. additionAfter the addition
  3. filtrationfiltered
  4. washThe filtrate is washed with 150 milliliters of 2N sodium hydroxide, water and 2N sodium hydroxide
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customfinally evaporated in vacuo
  7. customto yield an oil
  8. customThe oil is crystallized from ether

Sources & evidence

ORD record
ord-26c77f74c6f64e92b9bd3df7caa7064a
Source dataset
uspto-grants-1986_04
Patent number
US04582848

Reaction notes

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