Water → HCID 22619805, compound

HRID 840567Notes

Reaction equation

HRID 840567 reaction equation
[O:1]([S:8]([C:11]1[CH:20]=[C:19]2[C:14]([NH:15][CH2:16][C:17](=[O:21])[NH:18]2)=[CH:13][CH:12]=1)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][C:23]([CH3:27])=[CH:24][CH2:25]Br.O>CN(C)C(=O)C>[CH3:22][C:23]([CH3:27])=[CH:24][CH2:25][N:15]1[C:14]2[C:19](=[CH:20][C:11]([S:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)(=[O:9])=[O:10])=[CH:12][CH:13]=2)[NH:18][C:17](=[O:21])[CH2:16]1

Participants

5

Reactant 3

HCID 962WaterHCID 700922-Butene, 1-bromo-3-methyl-HCID 22619825HCID 22619825, compound

Product 1

HCID 22619805HCID 22619805, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

7-Phenoxysulfonyl-3,4-dihydroquinoxalin-2(1H)-one (1.52 g, 5.0 mmol) in 20 ml of N,N-dimethylacetamide was stirred for 8 hours at 100° C. with 2 ml of 3-methyl-2-buten-1-yl bromide. After cooling, the mixture was treated with water and extracted with ethyl acetate. The solution was dried using magnesium sulfate and then concentrated, and the residue was chromatographed over a silica gel column using ethyl acetate/heptane=1:1. The fractions which contained the substance were evaporated on a rotary evaporator, and the product was subsequently stirred with pentane and filtered off with suction, melting point 132° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. customThe solution was dried
  4. concentrationconcentrated
  5. customthe residue was chromatographed over a silica gel column
  6. customwere evaporated on a rotary evaporator
  7. filtrationfiltered off with suction, melting point 132° C.

Sources & evidence

ORD record
ord-1eb93360804e4fc4828ea5fc95d0d200
Source dataset
uspto-grants-2002_04
Patent number
US06369057B1

Reaction notes

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