HCID 12510286, compound → HCID 12510288, compound

HRID 2050216Notes

Reaction equation

HRID 2050216 reaction equation
[C:1]12([O:11][C:12]3[CH:18]=[CH:17][C:15]([NH2:16])=[C:14]([CH2:19]SC)[CH:13]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2>[Ni].C(O)C>[C:1]12([O:11][C:12]3[CH:18]=[CH:17][C:15]([NH2:16])=[C:14]([CH3:19])[CH:13]=3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

4

Reactant 1

HCID 12510286HCID 12510286, compound

Product 1

HCID 12510288HCID 12510288, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

23.2 g. (0.0764 mole) of 4-(1-adamantyloxy)-2-(methylthiomethyl)-aniline was stirred for 2 hours with approximately 96 g. of Raney nickel in 600 ml. of absolute ethanol. The catalyst was filtered and the solvent was evaporated. Purification by chromatography on silica gel followed by recrystallization from CH2Cl2 -Skellysolve B afforded the desired product, a tan solid, m.p. 143.4°-145.1° C. The NMR spectrum was in accord with the assigned structure.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent was evaporated
  3. customPurification by chromatography on silica gel
  4. customfollowed by recrystallization from CH2Cl2 -Skellysolve B

Sources & evidence

ORD record
ord-8f0184fcc5aa4968b8b9b0187f33a2b3
Source dataset
uspto-grants-1980_04
Patent number
US04200588

Reaction notes

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