Hydrochloric Acid → Sulfamic acid 2-(8-quinolinyloxy)ethyl ester

HRID 1613397Notes

Reaction equation

HRID 1613397 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][CH2:12][CH2:13][OH:14])[CH:4]=[CH:3][CH:2]=1.[S:15](Cl)(=[O:18])(=[O:17])[NH2:16].Cl>C(#N)C.C(O)(C)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][CH2:12][CH2:13][O:14][S:15](=[O:18])(=[O:17])[NH2:16])[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24499Chlorosulfamic acidHCID 4596088-(2-Hydroxyethyloxy)quinoline

Product 1

HCID 19108706Sulfamic acid 2-(8-quinolinyloxy)ethyl ester

Reagents, catalysts & solvents 1

HCID 21921005Acetonitrile 2-propanolSolvent

Procedure

Using the procedure of Example 54, 5.4 g (0.029 mole) of 2-(8-quinolinyloxy)ethanol was reacted with sulfamoyl chloride. During work-up of the reaction, quite a bit of light-yellow material deposited out from the organic-aqueous system. 1H NMR of this material suggested that it might be a quaternary salt. The oily product obtained at the end of the work-up procedure weighed 2.7 g. This oil was dissolved in acetonitrile-isopropyl alcohol and acidified with 37% hydrochloric acid. The mixture was evaporated to almost dryness and then redissolved in methanol. To the solution was added ethyl acetate and most of the methanol was evaporated carefully. The light-yellow solid was collected and dried at 40° C. in vacuum overnight to give 2.4 g solid monohydrochloride, mp 138°-140° C.

Workup

  1. customDuring work-up of the reaction
  2. customThe oily product obtained at the end of the work-up procedure
  3. customThe mixture was evaporated to almost dryness
  4. dissolutionredissolved in methanol
  5. additionTo the solution was added ethyl acetate
  6. custommost of the methanol was evaporated carefully
  7. customThe light-yellow solid was collected
  8. customdried at 40° C. in vacuum overnight

Sources & evidence

ORD record
ord-e5d2a2ac7b054e73aeef60e904098f8e
Source dataset
uspto-grants-1993_03
Patent number
US05192785

Reaction notes

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