Sodium Methoxide → HCID 9816625, compound

HRID 1168752Notes

Reaction equation

HRID 1168752 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[S:6][C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH:17]C(=O)C(Cl)(Cl)Cl)[C:8]=2[N:24]=1)[CH3:2].C[O-].[Na+]>CO>[CH2:1]([O:3][CH2:4][C:5]1[S:6][C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:24]=1)[CH3:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 22648280N-(2-(ethoxymethyl)thiazolo[4,5-c]quinolin-4-yl)trichloroacetamide

Product 1

HCID 9816625HCID 9816625, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Trichloroacetyl isocyanate (0.7 mL) was added to a solution of 2-(ethoxymethyl)thiazolo[4,5-c]quinoline-5N-oxide (1.0 g) in dichloromethane (50 mL). The reaction mixture was stirred at ambient temperature for 2 hours and then concentrated under vacuum to provide N-(2-(ethoxymethyl)thiazolo[4,5-c]quinolin-4-yl)trichloroacetamide. The amide was taken up in methanol and then combined with 1 equivalent of sodium methoxide. The reaction mixture was stirred at ambient temperature for 30 minutes and then concentrated under vacuum. The reaction was run a second time using 2 g of the N-oxide. The products were combined and recrystallized from isopropanol to provide 2.25 g of 2-(ethoxymethyl)thiazolo[4,5-c]quinoline-4-amine as light yellow needles, m.p. 149-151° C. Analysis: Calculated for C13H13N3OS: % C, 60.21; % H, 5.05; % N, 16.20; Found: % C, 59.86; % H, 4.97; % N, 16.16.

Workup

  1. concentrationconcentrated under vacuum
  2. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-5e5b4dd98faa430f8b4f0169812b87a8
Source dataset
uspto-grants-2003_09
Patent number
US06627638B2

Reaction notes

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