Ethyl bromoacetate → HCID 22097159, compound

HRID 861498Notes

Reaction equation

HRID 861498 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[NH:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)(=[O:20])=[O:19])([O-:3])=[O:2].C([O-])(C)(C)C.[K+].Br[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37]>CN(C)C=O>[CH2:39]([O:38][C:36]([CH2:35][N:17]([C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:4]=1[N+:1]([O-:3])=[O:2])[S:18]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)(=[O:20])=[O:19])=[O:37])[CH3:40]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 294498N-(2,4-Dinitronaphthalen-1-yl)-4-methylbenzene-1-sulfonamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 22097159HCID 22097159, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

60 g (155 mmol) of N-(2,4-dinitro-1-naphthyl)-4-methylphenylsulfonamide (J. Soc. Chem. 1935, 1855) were dissolved in 500 ml of anhydrous dimethylformamide under protective gas and 19.1 g (170 mmol) of potassium tert-butanolate were added a little at a time. The mixture was stirred at room temperature for about 30 minutes, and then 25.9 g (155 mmol) of ethyl bromoacetate dissolved in 50 ml of anhydrous dimethylformamide were added dropwise. The mixture was then heated at 100° C. for 90 minutes and, after cooling, poured into ice-water, and the aqueous phase was extracted with ethyl acetate. The organic phase was dried and concentrated under reduced pressure. The residue was heated with a mixture of 50 ml of toluene and 100 ml of ethanol and the resulting crystals were filtered off with suction to yield 55.7 g (76%) of the product. Melting point 106°-107° C.

Workup

  1. additionwere added a little at a time
  2. additionwere added dropwise
  3. temperatureThe mixture was then heated at 100° C. for 90 minutes
  4. temperatureafter cooling
  5. extractionthe aqueous phase was extracted with ethyl acetate
  6. customThe organic phase was dried
  7. concentrationconcentrated under reduced pressure
  8. temperatureThe residue was heated with a mixture of 50 ml of toluene and 100 ml of ethanol
  9. filtrationthe resulting crystals were filtered off with suction

Sources & evidence

ORD record
ord-f40fdcd342e746b8aba1601cdf317c28
Source dataset
uspto-grants-1998_02
Patent number
US05714489

Reaction notes

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