Sulfuric Acid → 5-[2-(2-Oxo-oxazolidin-3-yl)-ethyl]-1H-indole-2,3-dione

HRID 1094016Notes

Reaction equation

HRID 1094016 reaction equation
Cl.N1(CC2C=C(C=[C:15]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([CH2:24][CH2:25][N:26]5[CH2:30][CH2:29][O:28][C:27]5=[O:31])[CH:22]=4)[NH:17][C:16]3=[O:32])NC=2)CCOCC1.[OH:33]S(O)(=O)=O>>[O:31]=[C:27]1[N:26]([CH2:25][CH2:24][C:21]2[CH:22]=[C:23]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16](=[O:32])[C:15]3=[O:33])[CH2:30][CH2:29][O:28]1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 66636830HCID 66636830, compound

Product 1

HCID 666366885-[2-(2-Oxo-oxazolidin-3-yl)-ethyl]-1H-indole-2,3-dione

Conditions

Temperature
80 °C

Procedure

Concentrated H2SO4 (20 ml) is heated to 50° C. The compound obtained in Step D (25.24 mmoles) is added slowly in solid form, maintaining the temperature between 60 and 70° C. The reaction mixture is then stirred for one hour at 80° C. The mixture is brought to ambient temperature and then poured onto 200 g of crushed ice. After 30 minutes, the red solid formed is filtered off and washed intensively with ice-cold water; it is then dried in vacuo in the presence of P2O5 and at 40° C. overnight to yield the title product, which is used directly in the next Step.

Workup

  1. temperaturemaintaining the temperature between 60 and 70° C
  2. customis brought to ambient temperature
  3. waitAfter 30 minutes
  4. customthe red solid formed
  5. filtrationis filtered off
  6. washwashed intensively with ice-cold water
  7. dry with materialit is then dried in vacuo in the presence of P2O5 and at 40° C. overnight

Sources & evidence

ORD record
ord-9c150911faa141cba8f192b9595d68f1
Source dataset
uspto-grants-2012_03
Patent number
US08133889B2

Reaction notes

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