Hydrochloric Acid → HCID 10274459, compound

HRID 2100329Notes

Reaction equation

HRID 2100329 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:23])=[C:6]([S:8]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](Br)=[CH:14][CH:13]=2)(=[O:10])=[O:9])[CH:7]=1.Br[C:25]1[C:34]2[C:29](=CC=CC=2)[C:28]([NH2:35])=C[CH:26]=1.FC1C=CC(C)=C(S([Cl:46])(=O)=O)C=1.Cl>C(Cl)Cl.N1C=CC=CC=1>[ClH:46].[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:23])=[C:6]([S:8]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([C:34]3[CH2:29][CH2:28][NH:35][CH2:26][CH:25]=3)=[CH:14][CH:13]=2)(=[O:10])=[O:9])[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 1362865-Fluoro-2-methylbenzenesulphonyl chlorideHCID 68718199HCID 68718199, compound

Product 1

HCID 10274459HCID 10274459, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

5-Fluoro-2-methyl-N-[4-bromo-1-naphthyl]benzenesulfonamide—4-Bromo-1-naphthylamine (0.96 g, 4.33 mmol) was dissolved in DCM (10 mL) before pyridine (1 mL) was added. 5-Fluoro-2-methylbenzenesulfonyl chloride was added neat and the reaction mixture was stirred for 16 h. HCl (1 M, 1 mL) was added to the reaction mixture. The organic phase was filtered through a Silica plug using DCM as eluent. The solvent was evaporated. The obtained crude product was purified by flash-chromatography using MeOH (10%) in pentane, to give the desired product as a tar. To increase the purity, the product was purified by recrystallising (EtOAc/hexanes). This gave the product with a purity of 95%. 1H NMR (270 MHz, CDCl3) δ 8.22 (d, J=8.98 Hz, 1H), 7.92 (d, J=7.92 Hz, 1H), 7.64-7.51 (m, 4H), 7.25-7.23 (m, 1H), 7.21-7.05 (m, 2H), 6.84 (br.s, 1H, N—H), 2.55 (s, 3H); MS (ESI+) for C17 H13 Br F N O2 S m/z 394.263 (M+H)+.

Workup

  1. additionwas added
  2. filtrationThe organic phase was filtered through a Silica plug
  3. customThe solvent was evaporated
  4. customThe obtained crude product
  5. customwas purified by flash-chromatography

Sources & evidence

ORD record
ord-1b850612e7fa46b2b563eadd8ae01db0
Source dataset
uspto-grants-2009_08
Patent number
US07572787B2

Reaction notes

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