Bromine → N-(3-bromo-4-hydroxynaphthalen-1-yl)thiophene-2-sulfonamide

HRID 1258374Notes

Reaction equation

HRID 1258374 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:15])=[O:14])=[CH:4][CH:3]=1.[Br:21]Br>CN(C=O)C.C(OCC)(=O)C>[Br:21][C:3]1[CH:4]=[C:5]([NH:12][S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:15])=[O:14])[C:6]2[C:11]([C:2]=1[OH:1])=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

5

Reactant 2

HCID 24408BromineHCID 697391N-(4-hydroxynaphthalen-1-yl)thiophene-2-sulfonamide

Product 1

HCID 7718544N-(3-bromo-4-hydroxynaphthalen-1-yl)thiophene-2-sulfonamideYield 36.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

305.7 mg N-(4-hydroxynaphthalen-1-yl)thiophene-2-sulfonamide (3) was dissolved in 1 ml DMF, to which at 0° C. was added 320 mg Br2 in 1 ml dichloromethylene solution. After stirred at r.t. for 1 h, 558 μl TEA was added at 0° C. The reaction was stirred at r.t. overnight and diluted with ethyl acetate to 50 ml. The organic phase was washed with water and brine. Dried over Na2SO4, the organic phase was filtered and concentrated. The crude product was purified via flash chromatography (Hex/EtOAc gradient) affording an orange-red solid 140 mg (36.4%), m.p.: 128-130° C.

Workup

  1. stirringThe reaction was stirred at r.t. overnight
  2. washThe organic phase was washed with water and brine
  3. dry with materialDried over Na2SO4
  4. filtrationthe organic phase was filtered
  5. concentrationconcentrated
  6. customThe crude product was purified via flash chromatography (Hex/EtOAc gradient)

Sources & evidence

ORD record
ord-e70a62bbf0c34ee1af8b0bb449b5cebd
Source dataset
uspto-grants-2013_06
Patent number
US08466157B2

Reaction notes

Loading…