Thiophene-3-sulfonyl Chloride → Benzamide

HRID 931467Notes

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.S1C=CC(S(Cl)(=O)=O)=C1>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) (235 mg, 1.0 mmol) and 3-thienylsulfonyl chloride (208 mg, 1.1 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-5 (259 mg, 67%) as a white powder: mp (EtOAc) 207-210° C.; 1H NMR δ 10.40 (s, 1H, CONH), 8.93 (d, J=2.2 Hz, 1H, H-2″), 8.31 (dd, J=4.7, 1.5 Hz, 1H, H-6″), 8.23 (br t, J=6.3 Hz, 1H, NHSO2), 8.17-8.21 (m, 2H, H-2′, H-4″), 7.92 (dd, J=8.3, 1.7 Hz, 2H, H-2, H-6), 7.75 (dd, J=5.1, 1.3 Hz, 1H, H-5′), 7.42 (br d, J=8.4 Hz, 2H, H-3, H-5), 7.39 (dd, J=8.2, 4.7 Hz, 1H, H-5″), 7.35 (dd, J=5.1, 1.3 Hz, 1H, H-4′), 4.13 (d, J=6.3 Hz, 2H, CH2N); 13C NMR δ 165.5, 144.5, 141.9, 141.8, 140.5, 135.7, 132.9, 130.4, 129.0, 127.6 (2), 127.3 (2), 127.2, 125.1, 123.4, 45.7; MS m/z 374.6 (MH+, 100%). Anal. calcd for C17H15N3O3S2: C, 54.67; H, 4.05; N, 11.25. Found: C, 54.86; H, 3.95; N, 11.06%.

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-51226555ca344368b14b07d18f32b799
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296732B2

Reaction notes

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