Benzenesulfonyl chloride, 2,4-dichloro- → HCID 59864884, compound

HRID 2423274Notes

Reaction equation

HRID 2423274 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][CH3:22])=[O:20])=[CH:14][C:13]=2[O:23][CH3:24])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:25])[NH:6]2.[Cl:26][C:27]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=1[S:34](Cl)(=[O:36])=[O:35]>N1C=CC=CC=1>[Cl:26][C:27]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=1[S:34]([NH:1][C:2]1[C:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:14][C:13]=2[O:23][CH3:24])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:25])[NH:6]2)(=[O:36])=[O:35]

Participants

4

Reactant 2

HCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 59864814HCID 59864814, compound

Product 1

HCID 59864884HCID 59864884, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a room temperature solution of 1.3 (2.22 g, 6.52 mmol) dissolved in pyridine (14 mL) was added 2,4-dichlorobenzenesulfonyl chloride (1.76 g, 7.17 mmol). The resulting red solution was stirred at room temperature for 30 min., after which time LC-MS indicated no 13 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 ethyl acetate/hexane gradient, to afford a faint yellow solid. LC-MS ESI (pos.) m/z: 549.0 (100%), 551.0 (68%), 550.0 (28%) (M+H).

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 ethyl acetate/hexane gradient
  12. customto afford a faint yellow solid

Sources & evidence

ORD record
ord-9e55d51c5bdc46a3ac1ff86d02dad235
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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