Hydrochloric Acid → HCID 88465308, compound

HRID 1494001Notes

Reaction equation

HRID 1494001 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:19])(=[O:18])(=[O:17])[NH2:16].Cl>C(#N)C.C(O)(C)C>[ClH:19].[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 88465308HCID 88465308, compound

Reagents, catalysts & solvents 1

HCID 21921005Acetonitrile 2-propanolSolvent

Procedure

Using the procedure of Example 4, 5.4 g (0.029 mole) of 2-(8-quinolinyloxy)ethanol was reacted with sulfamoyl chloride. During work-up of the reaction, a 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, 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-0df22859efd143a8b3d37fe49b7cb49b
Source dataset
uspto-grants-1991_06
Patent number
US05025031

Reaction notes

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