Potassium Iodide → HCID 131715043, compound

HRID 980808Notes

Reaction equation

HRID 980808 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]12[CH:21]=[CH:20][CH:19]=[CH:18][CH:7]1[CH2:8][CH:9]2[C:10]([N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11].[I-].[K+].[N-:24]=[N+:25]=[N-:26].[Na+].OS([O-])=O.[Na+].C([O-])(O)=O.[Na+]>O.CN(C)C=O>[N:24]([CH2:2][CH2:3][CH2:4][O:5][C:6]12[CH:21]=[CH:20][CH:19]=[CH:18][CH:7]1[CH2:8][CH:9]2[C:10]([N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])=[N+:25]=[N-:26]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 33557Sodium AzideHCID 18331309HCID 18331309, compoundHCID 131715044HCID 131715044, compound

Product 1

HCID 131715043HCID 131715043, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 3-(3-chloropropoxy)-1-(1-piperidinylcarbonyl)benzocyclobutene (1.4 g), potassium iodide (4.5 g) and dimethylformamide (18.2 ml) is stirred at RT for 24 hours. Sodium azide (1.78 g) and H2O (1.82 ml) are added to the stirred mixture, which is heated for five hours at 75° C. The reaction mixture is poured into a solution of 10% NaHSO3 /NaHCO3 and extracted with methylene chloride. The organic layer is separated, washed, dried, filtered and evaporated in vacuo yielding the azide product as an oil.

Workup

  1. extractionextracted with methylene chloride
  2. customThe organic layer is separated
  3. washwashed
  4. customdried
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-098d48a00d3844b8a3a3b30bf4f7b06e
Source dataset
uspto-grants-1987_01
Patent number
US04639442

Reaction notes

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