Water → 1-Acridinamine

HRID 1486427Notes

Reaction equation

HRID 1486427 reaction equation
N([C:4]1[C:5]2[C:10]([N:11]=[C:12]3[C:17]=1[CH:16]=[CH:15][CH:14]=[CH:13]3)=[CH:9][CH:8]=[CH:7][CH:6]=2)=C=S.CC(N)[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O[C@H]3OC[C@@](O)(C)[C@H]([NH:43]C)[C@H]3O)[C@H](N)C[C@@H]2N)[C@H](N)CC1.CC(NC)[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O[C@H]3OC[C@@](O)(C)[C@H](NC)[C@H]3O)[C@H](N)C[C@@H]2N)[C@H](N)CC1.C[C@@]1(O)[C@H](NC)[C@@H](O)[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3O[C@H](CN)CC[C@H]3N)[C@@H](N)C[C@H]2N)OC1.OS(O)(=O)=O.O.OS(O)(=O)=O>CO>[NH2:43][C:6]1[C:5]2[C:10](=[N:11][C:12]3[C:17]([CH:4]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 820909-IsothiocyanatoacridineHCID 9855350Gentamicin Sulfate

Product 1

HCID 113521-AcridinamineYield 910.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent4×

Procedure

9-Isothiocyanatoacridin (100 mg) was dissolved in MeOH (5 mL), and added to the solution of gentamicin sulfate (250 mg) in 5 mL MeOH and some drops of water, followed by the solution of BaO (100 mg) in 5 mL MeOH. The suspension was stirred 30 min, neutralized with 3% H2SO4 in MeOH, filtered, evaporated to dryness and the residue was washed carefully with dichloromethane. Obtained 297 mg of yellow powder.

Workup

  1. filtrationfiltered
  2. customevaporated to dryness
  3. washthe residue was washed carefully with dichloromethane

Sources & evidence

ORD record
ord-5a66c58179864bdf88f5c0b726aeec75
Source dataset
uspto-grants-2016_08
Patent number
US09427406B2

Reaction notes

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