Ammonia → 2-Ethylthiazolo[4,5-c]quinolin-4-amine

HRID 1168745Notes

Reaction equation

HRID 1168745 reaction equation
[CH2:1]([C:3]1[S:4][C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[C:7]([NH:15]C(=O)C(Cl)(Cl)Cl)[C:6]=2[N:22]=1)[CH3:2].N>CO>[CH2:1]([C:3]1[S:4][C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[C:7]([NH2:15])[C:6]=2[N:22]=1)[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 22648275n-(2-Ethylthiazolo[4,5-c]quinolin-4-yl)trichloroacetamide

Product 1

HCID 99646202-Ethylthiazolo[4,5-c]quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(2-ethylthiazolo[4,5-c]quinolin-4-yl)trichloroacetamide (0.40 g) was suspended in a solution of ammonia in methanol (20 mL of 2M) and then stirred at ambient temperature for 30 minutes. The reaction mixture was concentrated under vacuum. The residue was washed with water and then dried to provide 0.19 g of crude product which was recrystallized from ethyl acetate/hexane to provide 2-ethylthiazolo[4,5-c]quinolin-4-amine as tan needles, m.p. 170-172° C. Analysis: Calculated for C12H11N3S: % C, 62.85; % H, 4.83; % N, 18.32; Found: % C, 62.58; % H, 4.78; % N, 18.08.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. washThe residue was washed with water
  3. customdried
  4. customto provide 0.19 g of crude product which
  5. customwas recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-5b76bb41453c48e489d851fa7a6170b1
Source dataset
uspto-grants-2003_09
Patent number
US06627638B2

Reaction notes

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