HCID 22492482, compound → HCID 22492464, compound

HRID 226174Notes

Reaction equation

HRID 226174 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 22492464HCID 22492464, compoundYield 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-fe960ab4eebc46f7b0e14c5372042f2c
Source dataset
uspto-grants-2009_07
Patent number
US07557140B2

Reaction notes

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