1-Adamantaneacetic acid → HCID 70523886, compound

HRID 904855Notes

Reaction equation

HRID 904855 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:10]=[C:9]([Cl:11])[C:8]([S:12](=[O:15])(=[O:14])[NH2:13])=[CH:7][C:5]=1[NH2:6].[C:16]12([CH2:26][C:27](O)=O)[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH2:17]1)[CH2:23]2>>[OH2:14].[C:16]12([CH2:26][C:27]3[NH:6][C:5]4[CH:7]=[C:8]([S:12](=[O:14])(=[O:15])[NH2:13])[C:9]([Cl:11])=[CH:10][C:4]=4[N:3]=3)[CH2:17][CH:18]3[CH2:24][CH:22]([CH2:21][CH:20]([CH2:19]3)[CH2:25]1)[CH2:23]2.[C:16]12([CH2:26][C:27]3[NH:6][C:5]4[CH:7]=[C:8]([S:12](=[O:14])(=[O:15])[NH2:13])[C:9]([Cl:11])=[CH:10][C:4]=4[N:3]=3)[CH2:17][CH:18]3[CH2:24][CH:22]([CH2:21][CH:20]([CH2:19]3)[CH2:25]1)[CH2:23]2

Participants

3

Reactant 2

HCID 1232211-Adamantaneacetic acidHCID 20477848HCID 20477848, compound

Product 1

HCID 70523886HCID 70523886, compoundYield 35.5%

Procedure

A mixture of 1.6 g of 2-amino-4-chloro-5-sulfamylaniline dihydrochloride and 1.6 g of 1-adamantane acetic acid was heated at 180°-200° for 5 hours. The mixture was cooled and the solid collected and ground into a fine powder; this was then added slowly to 100 ml of concentrated ammonium hydroxide with stirring. After stirring for twenty minutes, the solid was collected by filtration and then added to 150 ml of methanol, brought to a boil, charcoal added, and boiling continued for five minutes. The mixture was filtered through two sheets of filter paper, cooled, filtered through Celite, and then concentrated in vacuo to a dark pink solid. Recrystallization from acetonitrile provided 0.5 g of product, m.p. 203°-205°.

Workup

  1. temperaturewas heated at 180°-200° for 5 hours
  2. temperatureThe mixture was cooled
  3. customthe solid collected
  4. additionthis was then added slowly to 100 ml of concentrated ammonium hydroxide
  5. stirringAfter stirring for twenty minutes
  6. filtrationthe solid was collected by filtration
  7. additionadded to 150 ml of methanol
  8. additionadded
  9. filtrationThe mixture was filtered through two sheets of filter paper
  10. temperaturecooled
  11. filtrationfiltered through Celite
  12. concentrationconcentrated in vacuo to a dark pink solid
  13. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-94291372bdaa4c61b41100a9295ace6e
Source dataset
uspto-grants-1983_12
Patent number
US04420487

Reaction notes

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