Sodium hydride → HCID 12192069, compound

HRID 840362Notes

Reaction equation

HRID 840362 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].[H-].[Na+]>CN(C=O)C.C1COCC1>[Cl:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]2[O:12][CH:2]([CH3:7])[C:3](=[O:12])[NH:1][C:2]=2[CH:7]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 38948482-Amino-4-chloro-5-nitrophenol

Product 1

HCID 12192069HCID 12192069, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

7.52 g of 2-amino-4-chloro-5-nitrophenol is added to a mixture of 1.6 g of sodium hydride in 60 ml of DMF and mixed with 1.1 equivalents of D,L-2-bromopropionic acid ethyl ester in 20 ml of THF at 5° C. It is stirred for 4 hours. The mixture is poured onto water, extracted with ethyl acetate, the organic phase is dried with magnesium sulfate and concentrated by evaporation. 1.7 g of crude product, which is recrystallized from isopropyl ether, results. The yield is 72%.

Workup

  1. additionThe mixture is poured onto water
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic phase is dried with magnesium sulfate
  4. concentrationconcentrated by evaporation
  5. custom1.7 g of crude product, which is recrystallized from isopropyl ether
  6. customresults

Sources & evidence

ORD record
ord-e03e5dc6224c4e359df1d83ec126da23
Source dataset
uspto-grants-2002_04
Patent number
US06365736B1

Reaction notes

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