Methane → HCID 9815783, compound

HRID 393916Notes

Reaction equation

HRID 393916 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]([NH:14]C(=O)C(Cl)(Cl)Cl)[C:5]=2[N:21]=1.C[O-].[Na+].C>CO>[CH3:1][C:2]1[S:3][C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]([NH2:14])[C:5]=2[N:21]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 10942334Sodium MethoxideHCID 22648296HCID 22648296, compound

Product 1

HCID 9815783HCID 9815783, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Trichloroacetyl isocyanate (2.0 mL, 16.8 mmol) was added to a suspension of 2-methylthiazolo[4,5-c]quinoline-5N-oxide (3.03 g, 14.0 mmol) in dichloromethane (150 mL). The reaction mixture was stirred at ambient temperature for about 50 minutes. The dichloromethane was concentrated under vacuum to provide crude N-(2-methylthiazolo[4,5-c]quinolin-4-yl)trichloroacetamide. The amide was dissolved in methanol and then sodium methoxide (1 mL of 25% sodium methoxide in methanol) was added. The reaction was heated at reflux for 40 minutes then the methanol was evaporated under vacuum. The resulting brown solid was washed with water and dried to provide 2.85 g of crude product. This material was treated with charcoal and then recrystallized from ethyl acetate to provide 2-methylthiazolo[4,5-c]quinolin-4-amine as a solid, m.p. 184-186° C. Analysis: Calculated for C11H9N3S: % C, 61.37; % H, 4.21; % N, 19.52; Found % C, 61.48; % H, 4.17; % N, 19.60.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 40 minutes
  3. customthe methanol was evaporated under vacuum
  4. washThe resulting brown solid was washed with water
  5. customdried
  6. customto provide 2.85 g of crude product
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5c3a3f15601e4601b751b35fe885cca1
Source dataset
uspto-grants-2004_10
Patent number
US06809203B2

Reaction notes

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