Benzenesulfonyl chloride → HCID 68865402, compound

HRID 1725990Notes

Reaction equation

HRID 1725990 reaction equation
[NH2:1][C:2]1[C:11](/[CH:12]=[CH:13]/[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[C:3]=1[C:21]([O:23][CH3:24])=[O:22].[C:25]1([S:31](Cl)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>N1C=CC=CC=1>[C:17]([O:16][C:14](=[O:15])/[CH:13]=[CH:12]/[C:11]1[C:2]([NH:1][S:31]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:33])=[O:32])=[C:3]([C:21]([O:23][CH3:24])=[O:22])[C:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C:9]=2[CH:10]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 68865278HCID 68865278, compound

Product 1

HCID 68865402HCID 68865402, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of Example 476B (0.12 g, 0.36 mmol) in pyridine (1 mL) was treated with benzenesulfonyl chloride (0.071 g, 0.40 mmol), and stirred for 16 hours at ambient temperature. The mixture was concentrated, diluted with 1M NaHSO4 and extracted with dichloromethane. The extract was dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash chromatography eluting with 30% ethyl acetate/hexanes gave the desired product (0.12 g). MS (DCI) m/e 472 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with 1M NaHSO4
  3. extractionextracted with dichloromethane
  4. dry with materialThe extract was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash chromatography
  8. washeluting with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-a9e7384df65641cf9a6adf7d37baae5b
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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