Benzoic Acid → Acetophenone

HRID 2036276Notes

Reaction equation

HRID 2036276 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10](Cl)(=O)C(Cl)=O.Cl.CNOC.C[Mg]I>ClCCl.C(N(CC)CC)C.CN(C=O)C>[C:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:9])[CH3:10]

Participants

8

Reactant 4

HCID 243Benzoic AcidHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 178418373HCID 178418373, compound

Product 1

HCID 7410Acetophenone

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Scheme 9 depicts synthesis of 2-amino-4-aryl thiazoles of the formula (37) (wherein R4, R5, R6, R7, R8 and R9 are as defined above in description) which is prepared from acetophenones of the formula (36) using known approaches. Certain di- and tri-substituted acetophenones were not commercially available and they were prepared from the corresponding benzoic acid derivative of formula (32) in three steps. Thus, acid of formula (32) was converted to the corresponding acid chloride of formula (33) using oxalyl chloride in the presence of catalytic amounts of DMF in dry dichloromethane. The acid chloride of formula (33) was converted to corresponding Weinerb amide of formula (35) by treating with N,O-dimethylhydroxylamine hydrochloride of formula (34) in the presence of a suitable base such as triethylamine. The addition of methyl magnesium iodide to Weinreb amide of formula (35) afforded acetophenone derivative of formula (36).

Sources & evidence

ORD record
ord-66afddfe510d4a1fb1f06505189e4806
Source dataset
uspto-grants-2013_11
Patent number
US08575178B2

Reaction notes

Loading…