Sodium Hydroxide → HCID 18000861, compound

HRID 478158Notes

Reaction equation

HRID 478158 reaction equation
[Br:1][C:2]1([C:5]([NH:7][CH2:8][C:9](=O)[CH2:10][CH2:11][CH2:12][CH3:13])=O)[CH2:4][CH2:3]1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:16].[OH-].[Na+]>O1CCOCC1>[Br:1][C:2]1([C:5]2[S:16][C:9]([CH2:10][CH2:11][CH2:12][CH3:13])=[CH:8][N:7]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 18000839HCID 18000839, compound

Product 1

HCID 18000861HCID 18000861, compoundYield 193.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

500 mg of amide 86 and 212 mg of phosphorus pentasulfide are heated in 2 ml of dioxane for 25 minutes to 100° C. and, after cooling, poured into dilute sodium hydroxide solution. After extraction with ethyl acetate and drying on sodium sulfate, it is concentrated by evaporation, and the oily residue is chromatographed on silica gel with ethyl acetate/hexane. 240 mg of title compound 89 is obtained as a colorless oil.

Workup

  1. temperatureafter cooling
  2. extractionAfter extraction with ethyl acetate
  3. customdrying on sodium sulfate, it
  4. concentrationis concentrated by evaporation
  5. customthe oily residue is chromatographed on silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-1ee8179cfd804edb99ecbd3a549bd28c
Source dataset
uspto-grants-2003_11
Patent number
US06642218B2

Reaction notes

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