Benzenesulfonyl chloride → HCID 59811927, compound

HRID 2114033Notes

Reaction equation

HRID 2114033 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=3)[CH:9]=2)[NH:4][CH:3]=1.[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[Na+]>C1C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:20]1([S:26]([N:4]2[C:5]3=[N:6][CH:7]=[C:8]([C:11]4[CH:16]=[CH:15][C:14]([N:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=4)[CH:9]=[C:10]3[C:2]([I:1])=[CH:3]2)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 59811932HCID 59811932, compound

Product 1

HCID 59811927HCID 59811927, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 241BenzeneSolvent

Procedure

To a solution of 2 (6.00 g, 16.5 mmol) in benzene (100 mL) was added benzenesulfonyl chloride (4.85 mL, 38.0 mmol), tetra-n-butylammonium bromide (2.82 g, 8.76 mmol) and 50% aqueous NaOH (18.5 mL), and the reaction mixture was stirred overnight. The mixture was partitioned between water—benzene. The layers were separated and the aqueous layer was extracted with benzene (5×100 mL). The combined organic extracts were dried (MgSO4) and concentrated to give orange oil, which solidified on drying in vacuum. The solid was triturated with methanol (200 mL) for 0.5 h, filtered off, and washed with ice-cold methanol (3×50 mL) to give product 3 as a tan solid (5.32 g, 64%); 1H NMR (400 MHz, CDCl3) δ 3.01 (s, 6H), 6.81 (d, J=8.9 Hz, 2H), 7.45-7.60 (m, 4H), 7.59 (tt, J=14.8, 2.1 Hz, 1H), 7.74 (d, J=2.1 Hz, 1H), 7.86 (s, 1H), 8.24 (d, J=7.6 Hz, 2H), 8.64 (d, J=2.1 Hz, 1H); MS (CI) m/z 504.10 (MH+).

Workup

  1. customThe mixture was partitioned between water—benzene
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with benzene (5×100 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. customto give orange oil, which
  7. customon drying in vacuum
  8. customThe solid was triturated with methanol (200 mL) for 0.5 h
  9. filtrationfiltered off
  10. washwashed with ice-cold methanol (3×50 mL)

Sources & evidence

ORD record
ord-c962fb8c979c44c0b3a366a3ef122b99
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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