2-Thiophenesulfonyl chloride → Benzamide

HRID 1526852Notes

Reaction equation

HRID 1526852 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=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

4

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 167745724-(Aminomethyl)-N-(pyridin-3-YL)benzamide

Product 1

HCID 2331Benzamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 4-(aminomethyl)-N-(3-pyridinyl)benzamide (33) (256 mg, 1.1 mmol) and 2-thienylsulfonyl chloride (206 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 EtOAc, to give benzamide I-4 (318 mg, 75%) as a white powder: mp (EtOAc) 185-188° C.; 1H NMR δ 10.38 (s, 1H, NHCO), 8.93 (d, J=2.2Hz, 1 H, H-2″), 8.46 (br s, 1 H, NHSO2), 8.31 (dd, J=4.7, 1.5Hz, 1 H, H-6″), 8.19 (ddd, J=8.2, 2.5, 1.5Hz, 1 H, H-4″), 7.90-7.95 (m, 3 H, H-2, H-6, H-5′), 7.61 (dd, J=3.7, 1.3 Hz, 1 H, H-3′), 7.43 (br d, J=8.3Hz, 2 H, H-3, H-5), 7.39 (ddd, J=8.2, 4.7, 0.5 Hz, 1 H, H-5″), 7.18 (dd, J=5.0, 3.7Hz, 1 H, H-4′), 4.17 (s, 2 H, CH2N); 13C NMR δ 165.4, 144.4, 141.9, 141.5, 141.4, 135.7, 133.0, 132.4, 131.5, 127.6 (2), 127.5, 127.3 (2), 127.2, 123.4, 45.8; MS m/z 374.6 (MH+, 100%). Anal. calcd for C17H15N3O3S2: C, 54.67; H, 4.05; N, 11.25. Found: C, 55.23; H, 4.11; N, 11.32%.

Workup

  1. customThe solvent was evaporated
  2. stirringthe residue stirred in ice/water (20 mL) for 1 h
  3. filtrationThe precipitate was filtered
  4. washwashed with water (5 mL)
  5. customdried
  6. customThe crude solid was purified by column chromatography
  7. washeluting with EtOAc

Sources & evidence

ORD record
ord-daec2189a0024bf88b317633954be2a8
Source dataset
uspto-grants-2015_07
Patent number
US09085570B2

Reaction notes

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