2,4-Dichlorophenylacetonitrile → 4-Chloro-N-[2-(2,4-dichloro-phenyl)-propyl]-2-(2,6-difluoro-benzenesulfonylamino)-benzamide

HRID 2265219Notes

Reaction equation

HRID 2265219 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[S:9]([NH:12][C:13]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=O)(=[O:11])=[O:10].Cl.[Cl:24][C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=1[CH:32]([CH3:35])[CH2:33][NH2:34].ClC1C=C(Cl)C=CC=1CC#N>>[Cl:22][C:20]1[CH:19]=[CH:18][C:14]([C:15]([NH:34][CH2:33][CH:32]([C:26]2[CH:27]=[CH:28][C:29]([Cl:31])=[CH:30][C:25]=2[Cl:24])[CH3:35])=[O:17])=[C:13]([NH:12][S:9]([C:3]2[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])(=[O:10])=[O:11])[CH:21]=1

Participants

4

Reactant 3

HCID 805662,4-DichlorophenylacetonitrileHCID 687704442-(2,6-Difluoro-benzenesulfonylamino)-4-chloro-benzoic acidHCID 687728592-(2,4-Dichloro-phenyl)-propylamine hydrochloride

Product 1

HCID 116351584-Chloro-N-[2-(2,4-dichloro-phenyl)-propyl]-2-(2,6-difluoro-benzenesulfonylamino)-benzamide

Procedure

The title compound was prepared from 2-(2,6-difluoro-benzenesulfonylamino)-4-chloro-benzoic acid and 2-(2,4-dichloro-phenyl)-propylamine hydrochloride (prepared as in EXAMPLE 5, substituting 2,4-dichlorophenyl-acetonitrile in Part A) as in Example 1, Part C. HPLC: RT=11.20 min. MS (ESI−): mass calcd. for C22H17Cl3F2N2O3S, 533.8; m/z found, 533 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.62 (s, 1H), 7.73 (d, J=1.9, 1H), 7.52-7.45 (m, 1H), 7.40 (d, J=1.8, 1H), 7.28-7.25 (m, 2H), 7.18 (d, J=8.5, 1H), 7.01-6.96 (m, 3H), 6.05 (br m, 1H), 3.76-3.70 (m, 1H), 3.68-3.57 (m, 1H), 3.57-3.49 (m, 1H), 1.32 (d, J=6.8, 3H).

Workup

  1. customprepared as in EXAMPLE 5

Sources & evidence

ORD record
ord-4c1a2801bc764a30b8010a7ebabda8ef
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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