Methanol → HCID 21269271, compound

HRID 1194270Notes

Reaction equation

HRID 1194270 reaction equation
[N+:1]([O-:4])([OH:3])=[O:2].[C:5]12([CH2:14][CH:13]([N:15]3[C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:17]=[CH:16]3)[C:12]3[CH:24]=[CH:25][CH:26]=[CH:27][C:11]=3[O:10]1)[CH2:9][CH2:8][CH2:7][CH2:6]2.CO.[Br:30]Br>O>[N+:1]([O-:4])([OH:3])=[O:2].[Br:30][C:25]1[CH:26]=[CH:27][C:11]2[O:10][C:5]3([CH2:9][CH2:8][CH2:7][CH2:6]3)[CH2:14][CH:13]([N:15]3[C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:17]=[CH:16]3)[C:12]=2[CH:24]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24408BromineHCID 21269265HCID 21269265, compound

Product 1

HCID 21269271HCID 21269271, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 6.0 parts of methyl 1-[3,4-dihydrospiro-[2H-1-benzopyran-2,1'-cyclopentan]-4-yl]-1H-imidazole-5-carboxylate mononitrate in 135 parts of methanol were added 3.2 parts of bromine. The mixture was stirred for 1 hour at room temperature. The reaction mixture was poured into water and the whole was made alkaline. The product was extracted with 1,1'-oxybisethane. The extract was dried, filtered and evaporated. The residue was converted into the nitrate salt in a mixture of 16 parts of 2-propanone and 40 parts of 2,2'-oxybispropane. The salt was filtered off and dried in vacuo, yielding 4.4 parts (48.4%) of methyl 1-(6-bromo-3,4-dihydrospiro-[2H-1-benzopyran-2,1'-cyclopentan]-4-yl)-1H-imidazole-5-carboxylate mononitrate; mp. 162.3° C. (compound 1.63).

Workup

  1. extractionThe product was extracted with 1,1'-oxybisethane
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. additionThe residue was converted into the nitrate salt in a mixture of 16 parts of 2-propanone and 40 parts of 2,2'-oxybispropane
  6. filtrationThe salt was filtered off
  7. customdried in vacuo

Sources & evidence

ORD record
ord-c240cc8bbc664cfaaec6d88da77172ad
Source dataset
uspto-grants-1989_03
Patent number
US04813998

Reaction notes

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