Water → HCID 178468007, compound

HRID 1656021Notes

Reaction equation

HRID 1656021 reaction equation
[O:1]=[C:2]([CH2:7][C:8](=[O:10])[CH3:9])[CH2:3][CH2:4][C:5]#[N:6].[N-:11]=[N+:12]=[N-:13].[Li+].C(Cl)(Cl)Cl.CO.O>S(=O)(=O)(O)O.CN(C)C=O.C(O)(=O)C.CO.C(Cl)Cl>[O:1]=[C:2]([CH2:7][C:8](=[O:10])[CH3:9])[CH2:3][CH2:4][C:5]1[NH:13][N:12]=[N:11][N:6]=1

Participants

9

Reactant 4

HCID 962WaterHCID 88163Lithium azideHCID 197899544,6-DioxoheptanenitrileHCID 21584188Chloroform methanol

Product 1

HCID 178468007HCID 178468007, compound

Reagents, catalysts & solvents 4

HCID 1118Sulfuric AcidCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 10129899Acetic acid methanolSolvent

Procedure

A mixture of the 3,5-dioxohexylcyanide (2.78 gm; 20 mmole), lithium azide (1.08 gm; 22 mmole) and sulfuric acid (one drop) in 10 ml dry dimethylformamide is heated to 100-120 degrees. Progress of the reaction may be checked by TLC (silica gel; chloroform:methanol 97:3). When no starting material remaines, the reaction is cooled and 20 ml of water added. The reaction is taken to dryness under reduced pressure and the residue fractionated by silica gel flash column chromatography using methylene chloride: glac. acetic acid: methanol 100:3:3 as eluant. Fractions containing the product may be pooled and concentrated.

Workup

  1. temperatureis heated to 100-120 degrees
  2. customProgress of the reaction
  3. temperatureWhen no starting material remaines, the reaction is cooled
  4. additionFractions containing the product
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b592ed5104664430a447ceb3e59e8a11
Source dataset
uspto-grants-1993_10
Patent number
US05252603

Reaction notes

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