Hydrochloric Acid → Ethyl 1-ethyl-5-(2-thenoyl)oxindole-3-carboxylate

HRID 1788964Notes

Reaction equation

HRID 1788964 reaction equation
[Na].[CH2:2]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=[O:19])[C:14]3[S:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][CH:11]=2)[CH2:6][C:5]1=[O:20])[CH3:3].[C:21](=O)([O:25]CC)[O:22][CH2:23][CH3:24].Cl>[Cl-].[Na+].O.C(Cl)Cl.C(O)C>[CH2:2]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=[O:19])[C:14]3[S:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][CH:11]=2)[CH:6]([C:21]([O:22][CH2:23][CH3:24])=[O:25])[C:5]1=[O:20])[CH3:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 5360545SodiumHCID 137705281-Ethyl-5-(2-thenoyl)oxindole

Product 1

HCID 20189457Ethyl 1-ethyl-5-(2-thenoyl)oxindole-3-carboxylateYield 54.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To sodium ethoxide, formed by adding 2 g. of sodium metal to 58 ml. of ethanol, at 0° C. was added 7.84 g. (28.9 mmoles) of 1-ethyl-5-(2-thenoyl)oxindole followed by 10.24 g. (86.8 mmoles) of diethyl carbonate, and the reaction heated to 65° C. for 2 hours. The reaction mixture was poured into a cold mixture of 250 ml. 1N hydrochloric acid, 250 ml. of a saturated brine solution and 200 ml. of methylene chloride. The organic phase was separated, dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with diethyl ether and filtered. The filtrate was substantially concentrated to dryness under vacuum to give the desired product, 5.4 g. (54.4% yield).

Workup

  1. additionby adding 2 g
  2. additionThe reaction mixture was poured into a cold mixture of 250 ml
  3. customThe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with diethyl ether
  7. filtrationfiltered
  8. concentrationThe filtrate was substantially concentrated to dryness under vacuum

Sources & evidence

ORD record
ord-6c036ba3d462477b81ac6470a4fae0ac
Source dataset
uspto-grants-1987_08
Patent number
US04686224

Reaction notes

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