Sulfuric Acid → HCID 86652718, compound

HRID 244293Notes

Reaction equation

HRID 244293 reaction equation
C([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]1[C:25]2[C:26]3=[C:27]4[C:22](=[CH:23][CH:24]=2)[CH:21]=[CH:20][CH:19]=[C:18]4[CH:17]=[CH:16][C:15]3=[CH:14][CH:13]=1)=[O:5])C.[S:28](=[O:32])(=[O:31])([OH:30])O>>[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]1[CH:13]=[C:14]([S:28]([OH:32])(=[O:31])=[O:30])[C:15]2[CH:16]=[CH:17][C:18]3[C:27]4[C:26]=2[C:25]=1[CH:24]=[CH:23][C:22]=4[C:21]([S:28]([OH:30])(=[O:32])=[O:31])=[CH:20][C:19]=3[S:28]([OH:30])(=[O:32])=[O:31])([OH:3])=[O:5]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 86652717HCID 86652717, compound

Product 1

HCID 86652718HCID 86652718, compound

Conditions

Temperature
-30 °C

Procedure

1-(5-ethoxycarbonylpentyl)aminopyrene (1 g) was added in small portion to a stirred solution of 30% fuming sulfuric acid (8 mL) cooled to −30° C. After the addition, the solution was slowly warmed to room temperature and stirring continued at room temperature for 5 hours. The reaction mixture was poured over ice and the resulting precipitate was collected by suction filtration. The crude product was purified by HPLC on a C18 reverse phase column using triethylammonium acetate as the eluting buffer. The collected fractions containing the desired product were pooled and concentrated. The concentrate was acidified using HCl to precipitate out the product, which was then dried on a lyophilizer.

Workup

  1. additionAfter the addition
  2. temperaturethe solution was slowly warmed to room temperature
  3. additionThe reaction mixture was poured over ice
  4. filtrationthe resulting precipitate was collected by suction filtration
  5. customThe crude product was purified by HPLC on a C18 reverse phase column
  6. additionThe collected fractions containing the desired product
  7. concentrationconcentrated
  8. customto precipitate out the product, which
  9. customwas then dried on a lyophilizer

Sources & evidence

ORD record
ord-2ef272a009ad49f6a0b6bcd5dc7acc05
Source dataset
uspto-grants-2014_02
Patent number
US08658434B2

Reaction notes

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