Sulfuric Acid → HCID 21253733, compound

HRID 1531345Notes

Reaction equation

HRID 1531345 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][N:11]=[C:10]([CH2:13][CH2:14][S:15]([CH2:18][CH2:19][OH:20])(=[O:17])=[O:16])[N:9]=1.[S:21](=O)(=[O:24])([OH:23])[OH:22].OS(O)(=O)=O.O=S(=O)=O.C(=O)(O)[O-].[Na+].[Cl-].[K+]>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:21]([OH:24])(=[O:23])=[O:22])=[CH:4][C:3]=1[C:8]1[O:12][N:11]=[C:10]([CH2:13][CH2:14][S:15]([CH2:18][CH2:19][OH:20])(=[O:17])=[O:16])[N:9]=1

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 4873Potassium ChlorideHCID 24681Fuming sulfuric acidHCID 516892Sodium BicarbonateHCID 21253725HCID 21253725, compound

Product 1

HCID 21253733HCID 21253733, compound

Conditions

Temperature
40 °C

Procedure

59.4 g (0.2 mol) of 5-(2′-aminophenyl)-3-[2-(2-hydroxyethylsulfonyl)ethyl]-1,2,4-oxadiazole were added at 10-15° C. to 100% strength sulfuric acid and stirred in at 40° C. for 1 h. 240 ml of 24% strength by weight oleum were then added at 40° C. a little at a time over 20 h. After heating at 60° C. for 8 h, the reaction solution was poured onto ice, the pH was adjusted to pH 4-5 with sodium bicarbonate, and the product was salted out with 500 g of potassium chloride to afford 95.3 g of 5-(2′-amino-5′-sulfophenyl)-3-[2-(2-hydroxyethylsulfonyl)ethyl]-1,2,4-oxadiazole.

Workup

  1. temperatureAfter heating at 60° C. for 8 h
  2. additionthe reaction solution was poured onto ice

Sources & evidence

ORD record
ord-686a0cb940eb4bb2950eae328126ab22
Source dataset
uspto-grants-2001_03
Patent number
US06197941B1

Reaction notes

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