2-Chloro-5-pyridinesulfonyl chloride → Benzamide

HRID 931464Notes

Reaction equation

HRID 931464 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.ClC1N=CC(S(Cl)(=O)=O)=CC=1>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 27927922-Chloro-5-pyridinesulfonyl 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) (250 mg, 1.1 mmol) and 6-chloro-3-pyridinesulfonyl chloride (233 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 (0-30%) of MeOH/EtOAc, to give benzamide I-2 (279 mg, 63%) as a white powder: mp (MeOH/EtOAc) 226-228° C.; 1H NMR δ 10.36 (s, 1H, NHCO), 8.93 (d, J=2.2 Hz, 1H, H-2′), 8.75 (dd, J=2.6, 0.6 Hz, 1H, H-2″), 8.61 (br s, 1H, NHSO2), 8.32 (dd, J=4.6, 1.5 Hz, 1H, H-6′), 8.10-8.20 (m, 2H, H-4′, H-6″), 7.90 (br d, J=8.3 Hz, 2H, H-2, H-6), 7.72 (dd, J=8.4, 0.6 Hz, 1H, H-5″), 7.36-7.42 (m, 3H, H-3, H-5, H-5′), 4.19 (s, 2H, CH2N); 13C NMR δ 165.4, 153.6, 147.7, 144.6, 142.0, 141.2, 137.9, 136.6, 135.8, 133.1, 127.8 (2), 127.6 (2), 127.3, 125.0, 123.5, 45.7; MS m/z 404.0 (MH+, 100%), 406.0 (MH+, 60%). Anal. calcd for C18H15ClN4O3S: C, 53.67; H, 3.75; N, 13.91. Found: C, 53.37; H, 3.81; N, 14.03%.

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 a gradient (0-30%) of MeOH/EtOAc

Sources & evidence

ORD record
ord-ad075e1f062d48e6b5e200c04b527eec
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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