1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 73180807, compound

HRID 1916413Notes

Reaction equation

HRID 1916413 reaction equation
C(NC1C=CC(S([N:14]=[N+:15]=[N-])(=O)=O)=CC=1)(=O)C.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:20][CH:19]=1.C1CCN2C(=NCCC2)CC1>C(#N)C>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([C:24](=[N+:14]=[N-:15])[C:25]([O:27][CH3:28])=[O:26])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 104196Methyl 4-chlorophenylacetateHCID 51291854-Acetamidobenzenesulfonyl azide

Product 1

HCID 73180807HCID 73180807, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-acetamidobenzenesulfonyl azide (1.43 g, 5.96 mmol) and methyl 2-(4-chlorophenyl)acetate (1 g, 5.42 mmol) in acetonitrile (27 mL) was cooled to 0° C. DBU (0.907 g, 0.891 mL, 5.96 mmol) was then added dropwise to the reaction mixture. The mixture was allowed to stir over night, after which it was passed through a plug of silica and purified by column chromatography (EtOAc) to give methyl 2-(4-chlorophenyl)-2-diazoacetate (0.95 g, 83%) as a solid.

Workup

  1. custompurified by column chromatography (EtOAc)

Sources & evidence

ORD record
ord-90201119196541b0870045023616a8cf
Source dataset
uspto-grants-2013_12
Patent number
US08618097B2

Reaction notes

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