Hydrochloric Acid → HCID 86721862, compound

HRID 1049001Notes

Reaction equation

HRID 1049001 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9](Cl)(=[O:11])=[O:10])=[CH:4][CH:3]=1.N1C=CC=CC=1.[Cl:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23].Cl>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([NH:23][C:22]2[CH:24]=[CH:25][CH:26]=[C:20]([Cl:19])[CH:21]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 79323-ChloroanilineHCID 5987644-Bromobenzylsulfonyl chloride

Product 1

HCID 86721862HCID 86721862, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-bromo-phenyl)-methanesulfonyl chloride (1.4 g, 5.2 mmol) in DCM (20 mL) at room temperature was added pyridine (1.26 mL, 15.6 mmol) followed by 3-chloroaniline (1.1 mL, 10.4 mmol) and the reaction was stirred at room temperature for 3 hours. 1 M aqueous HCl was added and then extracted with DCM, filtered through a separator, concentrated, dry loaded onto silica and purified by silica gel column chromatography (0-100% DCM in cyclohexane) to give C-(4-bromo-phenyl)-N-(3-chloro-phenyl)-methanesulfonamide (0.61 g, 1.68 mmol). 1H NMR (300 MHz, CDCl3): δ 7.49 (d, 2H), 7.26 (m, 1H), 7.13-7.15 (m, 4H), 6.96-6.98 (m, 1H), 6.31 (s, 1H), 4.31 (s, 2H).

Workup

  1. extractionextracted with DCM
  2. filtrationfiltered through a separator
  3. concentrationconcentrated
  4. customdry loaded onto silica
  5. custompurified by silica gel column chromatography (0-100% DCM in cyclohexane)

Sources & evidence

ORD record
ord-33bdd149814d4ddb93f6e8de7c1adb9e
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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