Benzenesulfonyl chloride, 2,4-dichloro- → HCID 59864836, compound

HRID 2423280Notes

Reaction equation

HRID 2423280 reaction equation
[NH2:1][C:2]1[C:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:14][C:13]=2[O:24][CH3:25])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:27])[N:6]2[CH3:26].[Cl:28][C:29]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=1[S:36](Cl)(=[O:38])=[O:37]>N1C=CC=CC=1>[Cl:28][C:29]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=1[S:36]([NH:1][C:2]1[C:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:14][C:13]=2[O:24][CH3:25])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:27])[N:6]2[CH3:26])(=[O:38])=[O:37]

Participants

4

Reactant 2

HCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 59864880HCID 59864880, compound

Product 1

HCID 59864836HCID 59864836, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a room temperature solution of 3.3 (29 mg, 0.079 mmol) dissolved in pyridine (2 mL) was added 2,4-dichlorobenzenesulfonyl chloride (21 mg, 0.087 mmol). The resulting red solution was stirred at room temperature for 2 h, after which time HPLC indicated no 3.3 remained. The reaction solution was concentrated in vacuo on a rotary evaporator and the concentrate partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic separation was washed with water then brine. The organic extract was stirred over magnesium sulfate, filtered and the filtrate concentrated in vacuo on a rotary evaporator to afford an orange oil. The product was isolated by chromatography on silica gel, eluting with an ethyl acetate/hexane gradient, to afford a faint yellow oil. 1H NMR (500 MHz) (CDCl3) δ 7.71 (d, J=8.4 Hz, 1H); 7.48 (s, 1H); 7.04 (d, J=8.8 Hz, 1H); 6.88 (d, J=1.8 Hz, 1H); 6.70 (s, 1H); 6.59 (d, J=8.7 Hz, 1H); 6.53 (d, J=6.4 Hz, 1H); 6.52 (d, J=1.8 Hz, 1H); 6.16 (d, J=8.2 Hz, 1H); 4.19 (q, J=7.1 Hz, 2H); 3.86 (s, 3H); 3.64 (s, 3H); 3.59 (s, 2H); 2.48 (s, 3H) ppm.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo on a rotary evaporator
  2. customthe concentrate partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  3. customThe organic separation
  4. washwas washed with water
  5. extractionThe organic extract
  6. stirringwas stirred over magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo on a rotary evaporator
  9. customto afford an orange oil
  10. customThe product was isolated by chromatography on silica gel
  11. washeluting with an ethyl acetate/hexane gradient
  12. customto afford a faint yellow oil

Sources & evidence

ORD record
ord-3297f4cc7e8946e9927fde76968d1777
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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