Nitric Acid → HCID 86743491, compound

HRID 1638253Notes

Reaction equation

S[C:2]1[N:3]([CH:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][CH2:16]2)[C:4]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])=[CH:5][N:6]=1.[N+:25]([O-:28])([OH:27])=[O:26].[OH-].[Na+]>O>[N+:25]([O-:28])([OH:27])=[O:26].[C:9]1([C:7]([C:4]2[N:3]([CH:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:18][CH2:17][CH2:16]3)[CH:2]=[N:6][CH:5]=2)=[O:8])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 7 parts of [2-mercapto-1-(1,2,3,4-tetrahydro-1-naphthalenyl)-1H-imidazol-5-yl] phenylmethanone in 30 parts of water were added 30 parts of concentrated nitric acid. The whole was stirred for 15 minutes at 50° C. (intense reaction). After cooling, the reaction mixture was poured into crushed ice and treated with a sodium hydroxide solution. The product was extracted with trichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was converted into the nitrate salt in 1,1'-oxybisethane. The salt was filtered off and dried, yielding 0.9 parts (8.4%) of phenyl [1-(1,2,3,4-tetrahydro-1-naphthalenyl)-1H-imidazol-5-yl]methanone mononitrate; mp. 150.2° C. (compound 2.43).

Workup

custom(intense reaction)
temperatureAfter cooling
additionthe reaction mixture was poured
custominto crushed ice
extractionThe product was extracted with trichloromethane
washThe extract was washed with water
customdried
filtrationfiltered
customevaporated
filtrationThe salt was filtered off
customdried

Sources & evidence

ORD record: ord-cc26f8b132c14537812055b093bcb435
Source dataset: uspto-grants-1989_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04878940

Reaction notes

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