Hydrochloric Acid → 2-Benzylthiazolo[4,5-c]quinolin-4-amine hydrochloride

HRID 1168804Notes

Reaction equation

HRID 1168804 reaction equation
[CH2:1]([C:8]1[S:9][C:10]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[C:12]([NH:20]C(=O)C(Cl)(Cl)[Cl:23])[C:11]=2[N:27]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].Cl>CO.C(O)(C)C>[ClH:23].[CH2:1]([C:8]1[S:9][C:10]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[C:12]([NH2:20])[C:11]=2[N:27]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 22648314HCID 22648314, compound

Product 1

HCID 226482692-Benzylthiazolo[4,5-c]quinolin-4-amine hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 3776IsopropanolSolvent

Procedure

Trichloroacetyl isocyanate (1.2 mL, 10.3 mmol) was added to a solution of 2-benzylthiazolo[4,5-c]quinoline-5N-oxide (2.0 g, 6.8 mmol) in dichloromethane (100 mL). The reaction mixture was stirred at ambient temperature for 2 hours and then concentrated to provide crude N-(2-benzylthiazolo[4,5-c]quinolin-4-yl)trichloroacetamide. The amide was dissolved in methanol. Sodium methoxide (1 equivalent) was added. The reaction mixture was heated on a steam bath for 30 minutes and then allowed to cool to ambient temperature. The resulting precipitate was isolated by filtration and then suspended in a mixture of methanol and isopropanol. Hydrochloric acid (1 equivalent) was added and all of the solid dissolved initially. A white solid crystallized out. This material was isolated by filtration, washed with isopropanol and then dried to provide 1.5 g of 2-benzylthiazolo[4,5-c]quinolin-4-amine hydrochloride, m.p. 152-155° C. Analysis: Calculated for: C17H13N3S.HCl: %C, 62.28; %H, 4.30; %N, 12.82; Found: %C, 62.05; %H, 4.23; %N, 12.82.

Workup

  1. temperatureThe reaction mixture was heated on a steam bath for 30 minutes
  2. customThe resulting precipitate was isolated by filtration
  3. dissolutionall of the solid dissolved initially
  4. customA white solid crystallized out
  5. customThis material was isolated by filtration
  6. washwashed with isopropanol
  7. customdried

Sources & evidence

ORD record
ord-104613fdad014059b56a079a27913d67
Source dataset
uspto-grants-2003_09
Patent number
US06627640B2

Reaction notes

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