Tert-Butyl nitrite → HCID 20068390, compound

HRID 1638255Notes

Reaction equation

HRID 1638255 reaction equation
N[C:2]1[NH:6][CH2:5][N:4]([CH:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][C:8]2([CH3:17])[CH3:16])[C:3]=1[C:18](=[O:20])[CH3:19].N(OC(C)(C)C)=O>O1CCCC1>[CH3:16][C:8]1([CH3:17])[CH2:9][C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]1[N:4]1[C:3]([C:18](=[O:20])[CH3:19])=[CH:2][N:6]=[CH:5]1

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 178467248HCID 178467248, compound

Product 1

HCID 20068390HCID 20068390, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

13 Parts of [5-amino-3-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)1H-imidazol-4-yl]ethanone were dissolved in 167 parts of tetrahydrofuran. To the solution were added dropwise 7.7 parts of 2-methyl2-propyl nitrite. After stirring at room temperature for 1 hour, the reaction mixture was evaporated to dryness. The residue was purified by column chromatography over silica gel. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 1,1'-oxybisethane. The product was filtered off and dried, yielding 6.25 parts (51%) of [1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazol-5-yl]ethanone; mp. 69-70° C. (compound 1.10).

Workup

  1. customthe reaction mixture was evaporated to dryness
  2. customThe residue was purified by column chromatography over silica gel
  3. customThe pure fractions were collected
  4. customthe eluent was evaporated
  5. customThe residue was crystallized from 1,1'-oxybisethane
  6. filtrationThe product was filtered off
  7. customdried

Sources & evidence

ORD record
ord-965927f9a55643ec93abe0c6f0502701
Source dataset
uspto-grants-1989_11
Patent number
US04878940

Reaction notes

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