Sulfuric Acid → HCID 22743768, compound

HRID 2379672Notes

Reaction equation

HRID 2379672 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 is added to 63 ml of water with stirring and cooling. When the acid solution is at room temperature, 134 g (0.53M) of 6-chloroindoxyl-1,3-diacetate is added, portionwise, with stirring over a period of one hour keeping the temperature of the solution between 20° C. and 25° C. After stirring for 30 additional minutes after the addition is complete, the solution is poured onto 2 kilograms of ice. The ice is allowed to melt and the insoluble product is recovered by filtration and washed with cold water. This product is then protected from light and air and dried in a vacuum oven at room temperature. The yield of light yellow solid is about 110 g. This product is very unstable and may not be stored for long periods without decomposition. It is used immediately in the next step.

Workup

  1. temperaturecooling
  2. customis at room temperature
  3. stirringportionwise, with stirring over a period of one hour
  4. customthe temperature of the solution between 20° C. and 25° C
  5. stirringAfter stirring for 30 additional minutes
  6. additionafter the addition
  7. filtrationthe insoluble product is recovered by filtration
  8. washwashed with cold water
  9. customdried in a vacuum oven at room temperature
  10. waitmay not be stored for long periods without decomposition

Sources & evidence

ORD record
ord-732808f566be4b3d885dd0c948999421
Source dataset
uspto-grants-1994_11
Patent number
US05364767

Reaction notes

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