Diethyl Ether → Isatin

HRID 1413962Notes

Reaction equation

HRID 1413962 reaction equation
C[CH:2]1[C:10]2[C:5](=CC=[CH:8][CH:9]=2)[NH:4][C:3]1=S.CC(C)([O-:15])C.[K+].C([O:20][CH2:21][CH3:22])C>>[NH:4]1[C:3]2[C:22](=[CH:8][CH:9]=[CH:10][CH:2]=2)[C:21](=[O:20])[C:5]1=[O:15]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 14708632HCID 14708632, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 7054IsatinYield 32%

Procedure

According to the general procedure, 0.48 g of 3-methylthiooxindole and an equimolar quantity (E.Q.) of sublimed potassium t-butoxide in 200 ml of dry diethyl ether was aerated for 4 h at 0° C. and 20 h at 25° C. Acidification with 0.22 ml of conc. hydrochloric acid in 25 ml of water followed by extraction with ether, drying of the extracts over anhydrous magnesium sulfate, filtration, and evaporation of the filtrate gave an orange solid. Recrystallization from chloroform gave 0.13 g (32% yield) of pure isatin, mp 199°-200° C.

Workup

  1. extractionAcidification with 0.22 ml of conc. hydrochloric acid in 25 ml of water followed by extraction with ether
  2. dry with materialdrying of the extracts over anhydrous magnesium sulfate, filtration, and evaporation of the filtrate
  3. customgave an orange solid
  4. customRecrystallization from chloroform

Sources & evidence

ORD record
ord-fd85c6808b894cde88f413e900050fb5
Source dataset
uspto-grants-1981_02
Patent number
US04252723

Reaction notes

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