Phosphorus oxide (P4O10) → 5,6-Dihydrothieno[2,3-c]pyridin-7(4H)-one

HRID 1843829Notes

Reaction equation

HRID 1843829 reaction equation
C([O:3][C:4](=O)[NH:5][CH2:6][CH2:7][C:8]1[CH:12]=[CH:11][S:10][CH:9]=1)C.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O=P(Cl)(Cl)Cl>[S:10]1[C:9]2[C:4](=[O:3])[NH:5][CH2:6][CH2:7][C:8]=2[CH:12]=[CH:11]1

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 49670241Ethyl (2-(thiophen-3-yl)ethyl)carbamate

Product 1

HCID 218153465,6-Dihydrothieno[2,3-c]pyridin-7(4H)-oneYield 33.13%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
110 °C

Procedure

Using an analogous procedure and workup as described in Example 1, (2-thiophen-3-yl-ethyl)-carbamic acid ethyl ester (I-5c: 1.1 g, 5.527 mmol) in POCl3 (10 mL) was reacted with P2O5 (1.6 g, 11.05 mmol). The resulting mixture was stirred at 110° C. for 3 hours to afford the crude product. Purification by column chromatography on silica gel (1.5% methanol in DCM) afforded 280 mg of the product (33.13% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1.5% methanol in DCM)

Sources & evidence

ORD record
ord-096ce9b259234bd3bb613055afc1896c
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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