Phosphorus oxide (P4O10) → HCID 89964359, compound

HRID 1843944Notes

Reaction equation

C([O:3][C:4](=O)[NH:5][CH2:6][CH2:7][C:8]1[C:9]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:10]=2[S:11][CH:12]=1)C.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O=P(Cl)(Cl)Cl>>[F:17][C:15]1[CH:14]=[CH:13][C:10]2[S:11][C:12]3[C:4](=[O:3])[NH:5][CH2:6][CH2:7][C:8]=3[C:9]=2[CH:16]=1

Participants

Reactant 3

HCID 14812Phosphorus oxide (P4O10)

HCID 24813Phosphorus oxychloride

HCID 89964025HCID 89964025, compound

Product 1

HCID 89964359HCID 89964359, compoundYield 19.8%

Conditions

Temperature: 110 °C

Procedure

[2-(5-Fluoro-benzo[b]thiophen-3-yl)-ethyl]-carbamic acid ethyl ester (I-45d: 550 mg, 2.059 mmol) was reacted with P2O5 (461 mg, 4.11 mmol) and POCl3 (7 mL). The resulting mixture was refluxed at 110° C. for 2 hours to afford the crude product. Purification by column chromatography on silica gel (2% methanol in chloroform) afforded 90 mg of the product (19.78% yield).

Workup

customto afford the crude product
customPurification by column chromatography on silica gel (2% methanol in chloroform)

Sources & evidence

ORD record: ord-2aec7c030cdc4ac6a72afd8a94a66c15
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946260B2

Reaction notes

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