Ethyl Bromide → HCID 68548246, compound

HRID 2243110Notes

Reaction equation

HRID 2243110 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][CH:14]([CH3:19])[C:15]([O:17][CH3:18])=[O:16])(=[O:12])=[O:11])([O-:3])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:26](Br)[CH3:27]>CN(C)C=O>[CH2:26]([N:13]([S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])[CH:14]([CH3:19])[C:15]([O:17][CH3:18])=[O:16])[CH3:27]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 10796Cesium carbonateHCID 20791939HCID 20791939, compound

Product 1

HCID 68548246HCID 68548246, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 2-(2-nitrobenzenesulfonylamino)propionate (17 g; 59 mmol) is dissolved in 600 ml of dimethylformamide, and caesium carbonate (1.5 eq.; 88 mmol; 28.6 g) is then added. The reaction medium is stirred for 30 minutes at room temperature, followed by dropwise addition of ethyl bromide (4 eq.; 236 mmol; 17.6 ml) and the resulting mixture is stirred overnight at room temperature. The reaction medium is evaporated to dryness, taken up in dichloromethane, filtered and evaporated to dryness. The crude product is chromatographed on silica (eluting with dichloromethane) to give 17.1 g of the expected product.

Workup

  1. stirringthe resulting mixture is stirred overnight at room temperature
  2. customThe reaction medium is evaporated to dryness
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude product is chromatographed on silica (eluting with dichloromethane)

Sources & evidence

ORD record
ord-080a5f2f31314909896ac125ac46ac3c
Source dataset
uspto-grants-2010_03
Patent number
US07674803B2

Reaction notes

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