Formamide → 1-(4-Methyloxazol-5-yl)ethanone

HRID 129827Notes

Reaction equation

HRID 129827 reaction equation
Cl[CH:2]([CH2:6][CH:7]=O)[C:3](=[O:5])[CH3:4].[CH:9]([NH2:11])=[O:10]>C(O)=O>[CH3:7][C:6]1[N:11]=[CH:9][O:10][C:2]=1[C:3](=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 713FormamideHCID 137169073-Chloro-2,5-pentanedione

Product 1

HCID 110298391-(4-Methyloxazol-5-yl)ethanone

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Scheme IX illustrates the synthesis of compounds represented by Formula XVI. Reaction of a mixture of 3-chloro-2,5-pentanedione and formamide in refluxing formic acid yields 4-methyl-5-acetyloxazole. Reaction of the sodium salt of 4-methyl-5-acetyloxazole and diethyl oxalate in ethanol affords the corresponding ketoacetate. Reaction of the ketoacetate with hydrazine in refluxing ethanol yields 3-ethoxycarbonyl-5-[4-(methyl)oxazol-5-yl]pyrazole which is alkylated to yield isomers XXIIa and XXIIb. Substituting triethyl orthoacetate for triethyl orthoformate in the reaction described in Scheme V yields isomeric compounds represented by. Formula XVIIa and XVIIb ##STR12##

Workup

  1. customthe synthesis of compounds

Sources & evidence

ORD record
ord-ac4b96a863124209b6a8d7251913c03d
Source dataset
uspto-grants-1995_11
Patent number
US05470862

Reaction notes

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