Sodium Hydroxide → HCID 18000861, compound

HRID 1349372Notes

Reaction equation

HRID 1349372 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-a3355082ada24543bc079d372562b737
Source dataset
uspto-grants-2007_05
Patent number
US07211680B2

Reaction notes

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