HCID 22492482, compound → 3-(3-Oxoprop-1-ynyl)-N-phenylbenzenesulfonamide

HRID 2217697Notes

Reaction equation

HRID 2217697 reaction equation
[OH:1][CH2:2][C:3]#[C:4][C:5]1[CH:6]=[C:7]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1>CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(Cl)Cl>[O:1]=[CH:2][C:3]#[C:4][C:5]1[CH:6]=[C:7]([S:11]([NH:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 22492482HCID 22492482, compound

Product 1

HCID 224924643-(3-Oxoprop-1-ynyl)-N-phenylbenzenesulfonamideYield 86.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 159087TriacetoxyperiodinaneSolvent

Procedure

3-(3-Hydroxyprop-1-ynyl)-N-phenylbenzenesulfonamide (53a) (0.55 g, 1.9 mmol) was dissolved in a solution of Dess-Martin reagent in methylene chloride (0.157 g/ml) (8.2 ml) and the resultant mixture was stirred at ambient temperature for 30 min. The mixture was partitioned between water (50 ml) and ether (50 ml), and ether solution was washed successively with 5% Na2CO3, water, and dried (Na2SO4). The solvents were removed under reduced pressure to give the title compound (0.47 g, 72%) as an oil. The crude product 54a was used in the further step without an additional purification. 1H NMR (DMSO-d6, HMDSO) δ: 6.96-7.41 (5H, m, C6H5); 7.54-8.07 (4H, m, C6H4); 9.45 (1H, s, CH); 10.41 (1H, s, NH).

Workup

  1. customThe mixture was partitioned between water (50 ml) and ether (50 ml), and ether solution
  2. washwas washed successively with 5% Na2CO3, water
  3. dry with materialdried (Na2SO4)
  4. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-4625cfe9c7c74da1980a191d6ed9cec9
Source dataset
uspto-grants-2008_08
Patent number
US07407988B2

Reaction notes

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