Water → N-hydroxy-N-(3-benzo[b]thien-2-ylprop-2-enyl) acetamide

HRID 2351465Notes

Reaction equation

HRID 2351465 reaction equation
O1CCCCC1[O:7][NH:8][CH2:9][CH:10]=[CH:11][C:12]1[S:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[CH:13]=1.[O:21]1CCC[CH2:23][CH:22]1NO.S1C=C(C(Br)C=C)C2C=CC=CC1=2.O>CN(C=O)C>[OH:7][N:8]([CH2:9][CH:10]=[CH:11][C:12]1[S:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[CH:13]=1)[C:22](=[O:21])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 13168123Tetrahydropyranyl hydroxylamineHCID 198463353-Benzo[b]thienylbromoprop-2-eneHCID 86743434O-Tetrahydropyranyl-3-benzo[b]thien-2-ylprop-2-enyl hydroxylamine

Product 1

HCID 24103629N-hydroxy-N-(3-benzo[b]thien-2-ylprop-2-enyl) acetamideYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

O-Tetrahydropyranyl-3-benzo[b]thien-2-ylprop-2-enyl hydroxylamine. Tetrahydropyranylhydroxyl amine (0.51 g, 4.34 mmole) in DMF (10 mL) was added to a solution of 3-benzo[b]thienylbromoprop-2-ene (0.50 g, 1.98 mmole) in DMF (10 mL). After being allowed to stir for two hours the reaction was poured into water and extracted with ether. The organic layer was washed with NaHCO3 and brine. The organic layer was dried over MgSO4 and evaporated. The residue was chromatographed on silica gel eluting with 40% ether in hexanes to give the desired product as a yellow oil (66%).

Workup

  1. extractionextracted with ether
  2. washThe organic layer was washed with NaHCO3 and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated
  5. customThe residue was chromatographed on silica gel eluting with 40% ether in hexanes

Sources & evidence

ORD record
ord-18a37d57f339492d9e98a2d2ddc0525b
Source dataset
uspto-grants-1989_10
Patent number
US04873259

Reaction notes

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