N,N-dibenzyl formamide dimethyl acetal and N,N-dibenzyl chloromethylene iminium chloride: Two complementary reagents for the protection of primary amines as N,N-dibenzyl formamidines

Synthetic Communications

Volumn 29, Issue 2, 1999, Pages 167-174

  Vincent, Stéphane ^a   Lebeau, Luc ^a   Mioskowski, Charles ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

N,N DIBENZYLCHLOROMETHYLENE IMINIUM CHLORIDE; N,N DIBENZYLFORMAMIDE DIMETHYLACETAL; N,N DIBENZYLFORMAMIDINE; REAGENT; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; CHEMICAL REACTION; HYDROLYSIS; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 0033041681     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919908085753     Document Type: Article

References (25)

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23. Dimethyl formamide dimethyl acetal (5 eq.) and dibenzyl amine (3 eq.) are refluxed without solvent until the amine has completely disappeared when checked by TLC. Excess DMF dimethyl acetal is removed by two successive evaporations with xylene. Reaction with thiamine hydrochoride (1 eq.) is run in anhydrous methanol so as to solubilize the vitamin.
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25. The reaction can be run in anhydrous DMF with a comparable yield and without any formation of N,N-dimethyl formamidine.