Furan-2-sulfonyl Chloride → Benzamide

HRID 931470Notes

Reaction equation

NC[C:3]1[CH:17]=[CH:16][C:6]([C:7]([NH:9]C2C=NC=CC=2)=[O:8])=[CH:5][CH:4]=1.O1C=CC=C1S(Cl)(=O)=O>N1C=CC=CC=1>[C:7]([NH2:9])(=[O:8])[C:6]1[CH:16]=[CH:17][CH:3]=[CH:4][CH:5]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 4-(aminomethyl)-N-(3-pyridinyl)benzamide (33) (259 mg, 1.1 mmol) and 2-furanylsulfonyl chloride (209 mg, 1.2 mmol) in dry pyridine (10 mL) was stirred at 20° C. for 16 h. The solvent was evaporated and the residue stirred in ice/water (20 mL) for 1 h. The precipitate was filtered, washed with water (5 mL) and dried. The crude solid was purified by column chromatography, eluting with a gradient (0-10%) of MeOH/EtOAc, to give benzamide I-8 (248 mg, 61%) as a white powder: mp (EtOAc) 178-180° C.; 1H NMR δ 10.40 (s, 1H, CONH), 8.93 (d, J=2.2 Hz, 1H, H-2″), 8.69 (t, J=6.2 Hz, 1H, NHSO2), 8.31 (dd, J=4.7, 1.5 Hz, 1H, H-6″), 8.19 (ddd, J=8.3, 2.5, 1.5 Hz, 1H, H-4″), 7.94 (dd, J=1.8, 0.9 Hz, 1H, H-5′), 7.92 (br dd, J=8.3, 1.6 Hz, 2H, H-2, H-6), 7.37-7.43 (m, 3H, H-3, H-5, H-5″), 7.08 (dd, J=3.4, 0.9 Hz, 1H, H-3″), 6.65 (dd, J=3.4, 1.8 Hz, 1H, H-4″), 4.20 (d, J=6.2 Hz, 2H, CH2N); 13C NMR δ 165.5, 148.8, 146.8, 144.5, 141.9, 141.7, 135.7, 133.0, 127.7 (2), 127.2 (3), 123.4, 115.5, 111.3, 45.4; MS m/z 378.5 (MH+, 100%). Anal. calcd for C17H15N3O4S: C, 57.13; H, 4.23; N, 11.76. Found: C, 57.40; H, 4.19; N, 11.74%.

Workup

customThe solvent was evaporated
stirringthe residue stirred in ice/water (20 mL) for 1 h
filtrationThe precipitate was filtered
washwashed with water (5 mL)
customdried
customThe crude solid was purified by column chromatography
washeluting with a gradient (0-10%) of MeOH/EtOAc

Sources & evidence

ORD record: ord-6f12a34944194dfabdfe0ed784c683e8
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296732B2

Reaction notes

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