4-Chlorobenzenesulfonyl chloride → HCID 22993888, compound

HRID 2116540Notes

Reaction equation

HRID 2116540 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.CCN(CC)CC>CO.C1COCC1>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([O:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[C:6]([CH:12]=2)[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 9795116HCID 9795116, compound

Product 1

HCID 22993888HCID 22993888, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the aniline produced in Example 2 (82 mg, 0.32 mmol) in MeOH (3 mL) and THF (1 mL) was added 4-chlorobenzenesulfonyl chloride (74 mg, 0.35 mmol) followed by Et3N (89 μL, 0.64 mmol). After 20 minutes an additional amount of MeOH (1 mL) was added to aid in dissolving the reagents and the reaction mixture was allowed to stir overnight. At this time, the solvent was removed and the residue was dissolved into CH2Cl2. The resulting solution was washed three times with water and once with brine. The organic layer was evaporated and the resulting residue was purified by chromatography (1:1 hexane/diethyl ether) to provide 43.6 mg of the title compound (32% yield).

Workup

  1. dissolutionin dissolving the reagents
  2. customAt this time, the solvent was removed
  3. dissolutionthe residue was dissolved into CH2Cl2
  4. washThe resulting solution was washed three times with water
  5. customThe organic layer was evaporated
  6. customthe resulting residue was purified by chromatography (1:1 hexane/diethyl ether)

Sources & evidence

ORD record
ord-54dd71425a3f4b5c88e9b2dd1050f1b5
Source dataset
uspto-grants-2008_10
Patent number
US07439242B2

Reaction notes

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