Tetrahydrofuran → HCID 86635197, compound

HRID 554896Notes

Reaction equation

HRID 554896 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-])=O)[S:5][C:6]=1[C:7]([O-:9])=[O:8].[Sn](Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+].O1CC[CH2:31][CH2:30]1>>[NH2:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[NH:10][C:4]1[S:5][C:6]([C:7]([O:9][CH2:30][CH3:31])=[O:8])=[C:2]([CH3:1])[N:3]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 24479Stannous ChlorideHCID 86635198HCID 86635198, compound

Product 1

HCID 86635197HCID 86635197, compoundYield 77%

Conditions

Temperature
80 °C

Procedure

4-Methyl-2-(2-nitrophenylamino)thiazole-5-carboxylate (0.45 g, 1.46 mmol), tin(II) chloride dehydrate (1.66 g, 7.34 mmol) and tetrahydrofuran (25 mL) was added to a 100-mL round bottom flask. The mixture was refluxed at 75-85° C. for 3 h, cooled down to 0° C. and followed by the addition of saturated aqueous sodium carbonate solution (16 mL). The mixture was filtered through a celite cake and the filtrate was washed with saturated aqueous sodium carbonate solution (18 mL), water (2×15 mL) and brine (15 mL), dried over sodium sulfate, filtered and concentrated in vacuo to a small volume and triturated with diethyl ether. The solid was collected by filtration, washed with hexanes and dried in vacuo to afford ethyl 2-(2-aminophenylamino)-4-methylthiazole-5-carboxylate as a white solid (0.31 g, 77% yield): 1H NMR (300 MHz, CDCl3) δ 7.31-7.24 (m, 1H), 7.17-7.12 (m, 1H), 6.84-6.77 (m, 2H), 4.45-4.06 (m, 5H), 2.48 (s, 3H), 1.25 (t, J=7.05 Hz, 3H); MS (ES+) m/z 278.0 (M+1).

Workup

  1. temperaturecooled down to 0° C.
  2. filtrationThe mixture was filtered through a celite cake
  3. washthe filtrate was washed with saturated aqueous sodium carbonate solution (18 mL), water (2×15 mL) and brine (15 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a small volume
  7. customtriturated with diethyl ether
  8. filtrationThe solid was collected by filtration
  9. washwashed with hexanes
  10. customdried in vacuo

Sources & evidence

ORD record
ord-8adf80b298b54256b3a248c11e80ecb6
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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