Chlorosuccinimide → HCID 18760799, compound

HRID 433013Notes

Reaction equation

HRID 433013 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:8]2[N:9]=[N:10][N:11]([CH3:12])[C:7]=2[CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].ClN1C(=O)CCC1=O>C(COC)OC.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[K+].[K+]>[CH3:12][N:11]1[C:7]2[CH:6]=[C:5]([CH:3]=[O:2])[CH:14]=[CH:13][C:8]=2[N:9]=[N:10]1

Participants

8

Reactant 3

HCID 31398ChlorosuccinimideHCID 21226445Aluminium lithium hydrideHCID 54155113HCID 54155113, compound

Product 1

HCID 18760799HCID 18760799, compound

Reagents, catalysts & solvents 4

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolventHCID 20138282Sodium bicarbonate potassium carbonateSolvent

Procedure

3-Methyl-3H-benzotriazole-5-carboxylic acid methyl ester was taken on separately to the corresponding aldehydes by reduction with lithium aluminum hydride (1 equivalent) in anhydrous dimethoxyethane. The resulting alcohols were oxidized using 2,2,6,6-tetramethyl-1-piperidinyloxy free radical (1 equivalent), tetrabutylammonium chloride (1 equivalent), and N-chlorosuccinimide (1.3 equivalent) in methylene chloride and pH 8.6 sodium bicarbonate/potassium carbonate buffer to give 3-methyl-3H-benzotriazole-5-carbaldehyde.

Sources & evidence

ORD record
ord-9a516c6d8edd462ea0e47e3aafac5a7a
Source dataset
uspto-grants-2003_12
Patent number
US06664395B2

Reaction notes

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