Thionyl Chloride → HCID 59788880, compound

HRID 29241Notes

Reaction equation

[Cl:1][C:2]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:3]=1[C:4]([C:6]1[O:7][C:8]2[CH:17]=[C:16]([C:18]3[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=3)[CH:15]=[CH:14][C:9]=2[C:10]=1[C:11]([NH2:13])=O)=[O:5].O=S(Cl)Cl>>[Cl:1][C:2]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:3]=1[C:4]([C:6]1[O:7][C:8]2[CH:17]=[C:16]([C:18]3[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=3)[CH:15]=[CH:14][C:9]=2[C:10]=1[C:11]#[N:13])=[O:5]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 597889402-(2,4-Dichloro-benzoyl)-6-m-tolyl-benzofuran-3-carboxylic acid amide

Product 1

HCID 59788880HCID 59788880, compoundYield 13.2%

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-(2,4-Dichloro-benzoyl)-6-m-tolyl-benzofuran-3-carboxylic acid amide from Example 2 step 7 (46.2 mg, 0.11 mmol) and SOCl2 (3 mL) was heated at 80° C. for 15 h. The reaction was cooled down to rt and the solvent was removed under reduced pressure. The residue was purified by pre-HPLC to afford a yellow solid (5.9 mg, 13%) as product. 1H-NMR (CDCl3): δ 7.88 (d, J=8.3 Hz, 1H), 7.79 (s, 1H), 7.73 (dd, J=1.5, 8.3 Hz, 1H), 7.54 (d, J=1.5 Hz, 1H), 7.52 (d, J=8.3 Hz, 1H), 7.4 (dd, J=1.5, 8.3 Hz, 1H), 7.41 (m, 2H), 7.36 (t, 1H), 7.23 (d, J=8.3 Hz, 1H), 2.42 (s, 3H); LC-MS (MH+=406/408).

Workup

temperatureThe reaction was cooled down to rt
customthe solvent was removed under reduced pressure
customThe residue was purified by pre-HPLC

Sources & evidence

ORD record: ord-d94c1ec1227f44beae2c8eb8028e8dca
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07420066B2

Reaction notes

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