Hydrochloric Acid → HCID 28754924, compound

HRID 1417336Notes

Reaction equation

HRID 1417336 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:18][CH:17]=1.O.NN.Cl>C(O)C>[CH3:26][S:23]([NH:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][CH2:14][CH2:13][CH2:12][NH2:3])=[CH:17][CH:18]=1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 67693570HCID 67693570, compound

Product 1

HCID 28754924HCID 28754924, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 5.5 g of N-[4-[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propoxy]phenyl]methanesulfonamide in 200 ml of ethanol is treated with 1.5 ml of hydrazine hydrate and the mixture stirred and refluxed for 6 hours. A precipitate forms in 1 hour. After 6 hours, 5 ml of HCl is added and the mixture refluxed for 1 hour and allowed to stand at room temperature for 18 hours. The precipitate is collected, stirred with 50 ml of hot water and the insolubles washed with 50 ml of water. The combined water washes are evaporated in vacuo to a dry residue. The residue is dissolved in 100 ml of saturated sodium bicarbonate, treated with activated carbon, filtered and the filtrate acidified with acetic acid and concentrated in vacuo to 100 ml. The precipitate is collected, washed with 25 ml of cold water and dried to give a solid, m.p. 200° C.

Workup

  1. temperaturerefluxed for 6 hours
  2. waitAfter 6 hours
  3. temperaturethe mixture refluxed for 1 hour
  4. waitto stand at room temperature for 18 hours
  5. customThe precipitate is collected
  6. stirringstirred with 50 ml of hot water
  7. washthe insolubles washed with 50 ml of water
  8. customThe combined water washes are evaporated in vacuo to a dry residue
  9. dissolutionThe residue is dissolved in 100 ml of saturated sodium bicarbonate
  10. additiontreated with activated carbon
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo to 100 ml
  13. customThe precipitate is collected
  14. washwashed with 25 ml of cold water
  15. customdried
  16. customto give a solid, m.p. 200° C.

Sources & evidence

ORD record
ord-d5f289f66f274e4483340163fb0eb8bb
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

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