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

HRID 48262Notes

Reaction equation

HRID 48262 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-859fe9fed13e4ff3a94b9ac2c3fff8c1
Source dataset
uspto-grants-2004_03
Patent number
US06703402B2

Reaction notes

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