Sulfuric Acid → HCID 22743768, compound

HRID 248319Notes

Reaction equation

HRID 248319 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]([N:9]1[C:13]2[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=2[C:11]([O:19]C(C)=O)=[CH:10]1)=[O:8]>O>[Cl:18][C:15]1[CH:14]=[C:13]2[C:12]([C:11]([OH:19])=[CH:10][N:9]2[C:7](=[O:8])[CH3:6])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 117015591-acetyl-6-chloro-1H-indol-3-yl acetate

Product 1

HCID 22743768HCID 22743768, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 572 ml of concentrated sulfuric acid was added to 63 ml of water with stirring and cooling. When the acid solution was at room temperature, 134 g (0.53 M) of 6-chloroindoxyl-1,3-diacetate was added, portionwise, with stirring over a period of one hour keeping the temperature of the solution between 20° to 25° C. After stirring for 30 additional minutes after the addition was complete, the solution was poured onto 2 kg ice. The ice was allowed to melt and the insoluble product was filtered off and washed with cold water. This product was then protected from light and air and dried in a vacuum oven at room temperature. The yield of light yellow solid was 110 gm. This product was very unstable and could not be stored for long period without decomposition. It was used immediately in the next step.

Workup

  1. temperaturecooling
  2. customwas at room temperature
  3. stirringportionwise, with stirring over a period of one hour
  4. custombetween 20° to 25° C
  5. stirringAfter stirring for 30 additional minutes
  6. additionafter the addition
  7. filtrationthe insoluble product was filtered off
  8. washwashed with cold water
  9. customdried in a vacuum oven at room temperature
  10. waitcould not be stored for long period without decomposition

Sources & evidence

ORD record
ord-93a67200dae74fc79578076a1f71a0e9
Source dataset
uspto-grants-1993_05
Patent number
US05210022

Reaction notes

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