Ammonium Chloride → HCID 86755523, compound

HRID 2288579Notes

Reaction equation

HRID 2288579 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:17](=[S:25])[O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:6]3[C:11]([N:12]=2)=[CH:10][CH:9]=[C:8]([F:16])[CH:7]=3)[CH:3]=1.[NH4+].[Cl-]>CC(O)C.[Zn]>[F:1][C:2]1[CH:15]=[CH:14][C:13]2[NH:12][C:11]3[C:6](=[CH:7][C:8]([F:16])=[CH:9][CH:10]=3)[CH:5]([C:17](=[S:25])[O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 18006811HCID 18006811, compound

Product 1

HCID 86755523HCID 86755523, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 3776IsopropanolSolvent

Procedure

Phenyl 2,7-difluoroacridine-9-thiocarboxylate (1.2 g) was suspended in 2-propanol (125 mL) along with NH4Cl (4.57 g). Zinc (5.5 g) was added and the reaction mixture was warmed for 2.5 h followed by a 1.5 h period at room temperature. TLC of the reaction mixture showed complete conversion to a new material. The solution was filtered and the precipitate was washed with CH2Cl2. The filtrate was concentrated and the light orange residue was redissolved in CH2Cl2 and washed with water (2×100 mL). The organic layer was dried over Na2SO4 and concentrated to yield the crude product which was used without further purification. 1H NMR (CDCl3) δ5.12 (s, 1H), 6.19 (br s, 1H), 6.72-7.35 (m, 11H).

Workup

  1. temperaturethe reaction mixture was warmed for 2.5 h
  2. filtrationThe solution was filtered
  3. washthe precipitate was washed with CH2Cl2
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe light orange residue was redissolved in CH2Cl2
  6. washwashed with water (2×100 mL)
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2c063078fbd9487da104406a993594c2
Source dataset
uspto-grants-2000_07
Patent number
US06090571

Reaction notes

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