Hydrochloric Acid → HCID 15714023, compound

HRID 1709269Notes

Reaction equation

HRID 1709269 reaction equation
[C:1]1([S:7]([NH:10][CH2:11][CH2:12][C:13]2[CH:23]=[CH:22][C:16]([O:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:15][CH:14]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OC(=O)C)(=O)C.[N+:31]([O-])([OH:33])=[O:32].Cl>C(O)(=O)C>[C:1]1([S:7]([NH:10][CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:17][CH2:18][C:19]([OH:21])=[O:20])=[C:22]([N+:31]([O-:33])=[O:32])[CH:23]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 51550Sulotroban

Product 1

HCID 15714023HCID 15714023, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5 g of 4-(2-benzenesulfonylaminoethyl)phenoxyacetic acid are added to 30 ml of acetic anhydride, and 3 ml of a mixture of conc. nitric acid and acetic acid (1:2) are added thereto under ice-cooling and stirring. After the mixture is reacted for 4 hours at room temperature, the mixture is poured into a mixture of diluted hydrochloric acid and ice, extracted with ethyl acetate, dried and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform: ethanol=60:1) and recrystallized from a mixture of ethyl acetate and n-hexane. 3.70 g of 4-(2-benzenesulfonylaminoethyl)-2-nitrophenoxyacetic acid are obtained as colorless needles.

Workup

  1. additionare added
  2. temperatureunder ice-cooling
  3. customAfter the mixture is reacted for 4 hours at room temperature
  4. extractionextracted with ethyl acetate
  5. customdried
  6. customevaporated
  7. customto remove the solvent
  8. customThe residue is purified by silica gel column chromatography (solvent; chloroform: ethanol=60:1)
  9. customrecrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-8b9ec9cbda1d4aae8f1c220255187fc1
Source dataset
uspto-grants-1990_08
Patent number
US04948810

Reaction notes

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