Hydrochloric Acid → (E)-N-Hydroxy-3-[(toluene-4-sulfonyl)-1-H-pyrrol-3-yl]-acrylamide

HRID 870073Notes

Reaction equation

HRID 870073 reaction equation
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17](O)=[O:18])=[CH:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.C[Si](C)(C)[O:29][NH2:30].Cl>ClCCl.CN(C)C=O>[OH:29][NH:30][C:17](=[O:18])/[CH:16]=[CH:15]/[C:12]1[CH:13]=[CH:14][N:10]([S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:20])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 2734666O-(Trimethylsilyl)hydroxylamineHCID 66646287(E)-3-[1-(toluene-4-sulfonyl)-1H-pyrrol-3-yl]-acrylic acid2×

Product 1

HCID 11688099(E)-N-Hydroxy-3-[(toluene-4-sulfonyl)-1-H-pyrrol-3-yl]-acrylamideYield 20.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

0.231 g of (E)-3-[1-(toluene-4-sulfonyl)-1H-pyrrol-3-yl]-acrylic acid (compound A1) are dissolved in 8 ml of dichloromethane at room temperature. Then 50 μl of N,N-dimethylformamide (DMF) are added, 0.275 g of oxalic acid chloride dissolved in 2 ml of dichoromethane are added dropwise and stirred for 1.5 hour. To the solution are added 0.439 g of O-(trimethylsilyl)hydroxylamine and stirred for 15 minutes. Then 20 ml of aqueous hydrochloric acid (1 M strength) are added and extracted with ethyl acetate. The combined organic phase is dried over sodium sulfate. Afterwards it is filtered and evaporated under vacuo. The crude product is purified by silica gel flash chromatography using a gradient of dichloromethane and methanol from 98:2 to 6:4 to yield 0.050 g of the title compound as a white solid.

Workup

  1. additionare added dropwise
  2. stirringstirred for 15 minutes
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phase is dried over sodium sulfate
  5. filtrationAfterwards it is filtered
  6. customevaporated under vacuo
  7. customThe crude product is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-2152304e404a45b196e57a24e2d236bf
Source dataset
uspto-grants-2015_03
Patent number
US08969401B2

Reaction notes

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