Acetate → 4-t-Butylazo-4-azidopentyl chloroformate

HRID 866743Notes

Reaction equation

HRID 866743 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][C:8]([N:11]=[N:12][C:13]([CH3:16])([CH3:15])[CH3:14])(Cl)[CH3:9])(=[O:3])C.[N-:17]=[N+:18]=[N-:19].[Na+].C([O-])(=O)C.[OH-].[K+].[Cl:27]C([O-])=O.C(Cl)(Cl)=O>CO.CCCCC.N1C=CC=CC=1>[Cl:27][C:1]([O:4][CH2:5][CH2:6][CH2:7][C:8]([N:11]=[N:12][C:13]([CH3:16])([CH3:15])[CH3:14])([N:17]=[N+:18]=[N-:19])[CH3:9])=[O:3]

Participants

10

Reactant 6

HCID 175AcetateHCID 6371PhosgeneHCID 14797Potassium HydroxideHCID 33557Sodium AzideHCID 21226386Carbonochloridate2×HCID 233459014-t-Butylazo-4-chloropentyl acetate

Product 1

HCID 203182494-t-Butylazo-4-azidopentyl chloroformate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 8003PentaneSolvent2×

Procedure

This compound was prepared in the same manner as the 4-thiocyano derivative described in Example XXXI except that the 4-t-butylazo-4-chloropentyl acetate was added to a slight molar excess of sodium azide in 70% aqueous methanol. The acetate was saponified by the addition of excess KOH to the reaction. The alcohol was then converted to the chloroformate by adding a pentane solution of the alcohol and pyridine to a pentane solution of phosgene. After workup the infrared spectrum confirmed that the alcohol was converted to the chloroformate.

Sources & evidence

ORD record
ord-64c7ec934c094f4db383a48ff7ab6cfe
Source dataset
uspto-grants-1978_07
Patent number
US04101522

Reaction notes

Loading…