Sodium Carbonate → N-(4-methoxy-2-nitrophenyl)-2-methyl-5-oxazolemethanamine

HRID 1197818Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:20][C:21]1[O:25][C:24]([CH3:26])=[N:23][CH:22]=1>CN(C)C=O>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][CH2:20][C:21]2[O:25][C:24]([CH3:26])=[N:23][CH:22]=2)=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 33.63 parts of 1-amino-4-methoxy-2-nitrobenzene in 282 parts of N,N-dimethylformamide there were added 21.2 parts of sodium carbonate and a solution of 35.2 parts of 5-bromomethyl-2-methyloxazole in 94 parts of N,N-dimethylformamide. The whole was stirred for 20 hours at 70° C. and was then evaporated. The residue was taken up in water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2C2 /CH3OH 95:5). The eluent of the desired fraction was evaporated and the residue was crystallized from petroleum ether. The product was filtered off and dried, yielding 30 parts (57.0%) of N-(4-methoxy-2-nitrophenyl)-2-methyl-5-oxazolemethanamine (interm. 14).

Workup

customwas then evaporated
extractionthe product was extracted with dichloromethane
customThe extract was dried
filtrationfiltered
customevaporated
customThe residue was purified by column chromatography (silica gel
customThe eluent of the desired fraction was evaporated
customthe residue was crystallized from petroleum ether
filtrationThe product was filtered off
customdried

Sources & evidence

ORD record: ord-995e02637d7c430bbc66e014edbc1e75
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05278165

Reaction notes

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