Ammonium Chloride → HCID 69337169, compound

HRID 2395927Notes

Reaction equation

HRID 2395927 reaction equation
FC(F)(F)S([O-])(=O)=O.[CH3:9][N+:10]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([C:24]([N:26]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[NH:27][S:28]([C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)(=[O:30])=[O:29])=[O:25])=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[CH:15]2.[Cl-].[NH4+]>C(O)C.C(Cl)Cl.[Zn]>[CH3:9][N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]([C:24]([N:26]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[NH:27][S:28]([C:31]2[CH:32]=[CH:33][C:34]([CH3:37])=[CH:35][CH:36]=2)(=[O:30])=[O:29])=[O:25])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:23]1=2

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 18987970HCID 18987970, compound

Product 1

HCID 69337169HCID 69337169, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

10-Methyl-N-(phenyl)-N-(p-toluenesulfonamido)acridinium-9-carboxamide trifluoromethanesulfonate (10 mg, 0.0016 mmol) was suspended in absolute ethanol (10 mL) and solution was refluxed for 15 min to obtain a clear solution. Ammonium chloride (88 mg, 1.6 mmol) was added by portions to thesolution followed by zinc (108 mg, 1.6 mmol). The yellow color of solution disappeared immediately after the addition of zinc. Colorless solution wasrefluxed for 2 h. TLC of reaction mixture showed complete conversion to a non-polar material. Solution was filtered and precipitate was washed with ethanol (3×20 mL). Solution was concentrated to obtain an off-white solid which was redissolved in methylene chloride and washed with water (2×15 mL). Organic layer was dried over Na2SO4 and concentrated to yield the crude product which was purified by preparative TLC using (30% ethyl acetate:hexane) Pure product was obtained as an off-white solid. 1HNMR (CDCl3) δ2.40 (s, 3H), 3.18 (s, 3H) 5.00 (s, 1H), 6.76-7.77 (m, 12H).

Workup

  1. temperaturesolution was refluxed for 15 min
  2. customto obtain a clear solution
  3. customTLC of reaction mixture
  4. filtrationSolution was filtered
  5. washprecipitate was washed with ethanol (3×20 mL)
  6. concentrationSolution was concentrated
  7. customto obtain an off-white solid which
  8. washwashed with water (2×15 mL)
  9. dry with materialOrganic layer was dried over Na2SO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-9bfdd76987d2408a9cd36316a53485dd
Source dataset
uspto-grants-1996_02
Patent number
US05491072

Reaction notes

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