Iodine → HCID 90314654, compound

HRID 1524053Notes

Reaction equation

HRID 1524053 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([S:16]([NH:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])=[O:17])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][C:5]=1[F:24])(=O)[CH3:2].II.[NH2:27][C:28]([NH2:30])=[S:29]>CCO>[NH2:30][C:28]1[S:29][CH:2]=[C:1]([C:4]2[CH:9]=[CH:8][C:7]([C:10]3[C:11]([S:16]([NH:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])=[O:17])=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:6][C:5]=2[F:24])[N:27]=1

Participants

5

Reactant 3

HCID 807IodineHCID 2723790ThioureaHCID 90313766HCID 90313766, compound

Product 1

HCID 90314654HCID 90314654, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4′-acetyl-N-tert-butyl-3′-fluorobiphenyl-2-sulfonamide (100 mg, 0.29 mmol), iodine (94.6 mg, 0.37 mmol), thiourea (44.01, 0.57 mmol) in EtOH (1.1 mL) was heated at 100 Celcius for 48 h. The reaction mixture was cooled to rt and the precipitate collected by filtration thus providing the title compound. MS (ESI): mass calcd. for C19H20FN3O2S2, 405.10; m/z found, 406.2 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.71 (s, 2H), 8.19 (d, J=7.9, 1H), 7.94 (m, 1H), 7.59 (m, 1H), 7.54 (dd, J=11.6, 3.8, 1H), 7.44 (dd, J=12.1, 1.6, 1H), 7.38 (dd, J=8.1, 1.7, 1H), 7.33 (dd, J=7.5, 1.3, 1H), 6.96 (d, J=1.3, 1H), 1.08 (s, 9H).

Workup

  1. filtrationthe precipitate collected by filtration

Sources & evidence

ORD record
ord-df13f47d3e5345298425f04f4d23f41e
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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