Triethylamine → HCID 59679873, compound

HRID 1393754Notes

Reaction equation

HRID 1393754 reaction equation
[N+:1]([C:4]1[S:8][C:7]([C:9]2[O:10][C:11]3[CH:16]=[CH:15][N:14]=[CH:13][C:12]=3[N:17]=2)=[CH:6][CH:5]=1)([O-])=O.[NH4+].[Cl-].C(OCC)(=O)C.CCN(CC)CC>CO.O.[Fe]>[O:10]1[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[N:17]=[C:9]1[C:7]1[S:8][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 59680236HCID 59680236, compound

Product 1

HCID 59679873HCID 59679873, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

2-(5-nitrothiophen-2-yl)oxazolo[4,5-c]pyridine (1.775 g, 7.2 mmol), iron powder (2.108 g, 36.0 mmol) and NH4Cl (3.081 g, 57.6 mmol) were refluxed in CH3OH/H2O (4:1, 360 mL) for 6 h. The mixture was filtered and the filtration was evaporated in vacuo. The residue was purified by chromatography on silica gel eluted with petroleum ether:ethyl acetate:Et3N=160:40:1 to afford 5-(oxazolo[4,5-c]pyridin-2-yl)thiophen-2-amine as a yellow solid (1.1 g, yield: 70%). 1HNMR (400 MHz, DMSO-d6) δ: 8.83 (1H, s), 8.41 (1H, d, J=4.8 Hz), 7.67 (1H, d, J=4.8 Hz), 7.57 (1H, d, J=4.4 Hz), 6.91 (2H, s), 6.03 (1H, d, J=4.4 Hz); MS (ESI) calcd. for C10H7N3OS (m/z): 217, found: 218 [M+1]+.

Workup

  1. filtrationThe mixture was filtered
  2. filtrationthe filtration
  3. customwas evaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel
  5. washeluted with petroleum ether

Sources & evidence

ORD record
ord-75d86c083ac84998ae31369705909414
Source dataset
uspto-grants-2008_03
Patent number
US07345178B2

Reaction notes

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