Thionyl Chloride → HCID 86062305, compound

HRID 1925336Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C:17]([C:21]([OH:23])=O)=[CH:16][CH:15]=[CH:14]3)[CH:7]=[CH:6][N:5]=1)(=[O:3])[NH2:2].O=S(Cl)[Cl:26]>C1(C)C=CC=CC=1>[C:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C:17]([C:21]([Cl:26])=[O:23])=[CH:16][CH:15]=[CH:14]3)[CH:7]=[CH:6][N:5]=1)(=[O:3])[NH2:2]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 6-(2-carbamoylpyridin-4-yloxy)-1-napthoic acid (Step a, 1.0 g, 3.2 mmol) and SOCl2 (600 μL, 8.1 mmol) in toluene (25 mL, Aldrich) was heated at 110° C. for 7 h. The resulting solution was concentrated under reduced pressure and azeotroped from toluene (3×10 mL) to provide the title compounds as a yellow solid. MS (ESI, pos. ion) m/z: 327.5 (M+1). Mass Calc'd for C17H11ClN2O3: 326.73.

Workup

concentrationThe resulting solution was concentrated under reduced pressure
customazeotroped from toluene (3×10 mL)

Sources & evidence

ORD record: ord-5f30482f12c84632b8b7d75b44ef8731
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178557B2

Reaction notes

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