Stannous Chloride → 3-Chloro-5-(thiazol-5-yl)aniline

HRID 2375888Notes

Reaction equation

HRID 2375888 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[S:15][CH:14]=[N:13][CH:12]=2)[CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.[Sn](Cl)Cl.C([O-])(O)=O.[Na+]>>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([C:11]2[S:15][CH:14]=[N:13][CH:12]=2)[CH:3]=1

Participants

4

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 587099825-(3-Chloro-5-nitrophenyl)thiazole

Product 1

HCID 587099553-Chloro-5-(thiazol-5-yl)aniline

Conditions

Temperature
90 °C

Procedure

To a solution of 5-(3-chloro-5-nitrophenyl)thiazole (0.120 g, 0.499 mmol) inethanol (5 mL) was added tin dichloride (0.9555 g, 4.986 mmol). The mixture was stirred at 90° C. for 1.5 h. After cooling to rt, sat. NaHCO3 (aq) was added dropwise to adjust the pH to 9-10. The resulting suspension was filtered through a Celite pad. The filtrate was concentrated to dryness in vacuo to afford the title compound, which was used directly in the next step without purification. 1H-NMR (CD3OD, 400 MHz): δ=6.67 (t, J=2.0 Hz, 1H), 6.85 (t, J=1.6 Hz, 1H), 6.88 (t, J=1.6 Hz, 1H), 8.10 (s, 1H), 8.94 (s, 1H). MS (ES+): m/z 211.10 (MH+, 35Cl), 213.12 (MH+, 37Cl). HPLC: tR=2.92 min (ZQ2000, polar—5 min).

Workup

  1. temperatureAfter cooling to rt
  2. filtrationThe resulting suspension was filtered through a Celite pad
  3. concentrationThe filtrate was concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-6ed5c3b3543f44d0a87ee01b79edc35f
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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