Hydrochloric Acid → HCID 9804615, compound

HRID 1818058Notes

Reaction equation

HRID 1818058 reaction equation
C(N(CC)CC)C.[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:26][C:27]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:28]=2[CH:29]=[CH:30][CH:31]=[C:32]3[S:37](Cl)(=[O:39])=[O:38])(=[O:25])=[O:24])=[CH:19][CH:18]=1.Cl>O1CCCC1>[CH2:8]([NH:15][S:37]([C:32]1[C:33]2[C:28](=[C:27]([O:26][S:23]([C:20]3[CH:21]=[CH:22][C:17]([CH3:16])=[CH:18][CH:19]=3)(=[O:25])=[O:24])[CH:36]=[CH:35][CH:34]=2)[CH:29]=[CH:30][CH:31]=1)(=[O:38])=[O:39])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 8471TriethylamineHCID 18948960HCID 18948960, compound

Product 1

HCID 9804615HCID 9804615, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.17 ml, 1.2 mmol) was added to benzylamine (117.9 mg, 1.1 mmol) dissolved in tetrahydrofuran (5 ml). After the solution was cooled in the ice bath, 5-{[(4-methylphenyl)sulfonyl]oxy}naphthalene-1-sulfonyl chloride (396.9 mg, 1.2 mmol) was added, and the mixture was stirred at room temparature for 1 hour. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (eluent; n-hexane : ethyl acetate=2:1) and crystallized (ethyl acetate/hexane) to give the title compound as a white crystal (398.8 mg, 85.3%).

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washAfter the organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe residue obtained by evaporation of the solvent under reduced pressure
  6. customwas purified by column chromatography on silica gel (eluent; n-hexane : ethyl acetate=2:1)
  7. customcrystallized (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3d92748b370c479babb52ac8e8f208ee
Source dataset
uspto-grants-2009_10
Patent number
US07598418B2

Reaction notes

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