Hydrochloric Acid → HCID 3844502, compound

HRID 2265186Notes

Reaction equation

HRID 2265186 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:12])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].N1C=CC=CC=1.[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[S:27](Cl)(=[O:29])=[O:28].Cl>C(Cl)Cl>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([Cl:1])=[CH:3][C:4]=1[NH:12][S:27]([C:21]1[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:20]=1[F:19])(=[O:29])=[O:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 80001Methyl 4-chloroanthranilateHCID 27342732,4-Difluorobenzenesulfonyl Chloride

Product 1

HCID 3844502HCID 3844502, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-chloroanthranilate (0.50 g, 2.7 mmol) and pyridine (0.87 mL, 10.8 mmol) in DCM (10 mL) at rt was added 2,4-difluorobenzenesulfonyl chloride (0.64 g, 3.0 mmol). The mixture was stirred overnight at rt, poured into 1 N HCl, and extracted with DCM (3×). The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (EtOAc/hexanes) to provide 0.69 g (70%) of the desired sulfonamide as a solid. 1H NMR (400 MHz, CDCl3): 11.02 (s, 1H), 8.07-8.00 (m, 1H), 7.91 (d, J=8.6, 1H), 7.64 (d, J=2.0, 1H), 7.04-6.98 (m, 1H), 7.02 (dd, J=8.6, 2.0, 1H), 6.93-6.86 (m, 1H), 3.94 (s, 3H).

Workup

  1. extractionextracted with DCM (3×)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-f35d5a9cfd6445389864cb37e32bf38b
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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