Chlorotrimethylsilane → HCID 20068396, compound

HRID 1638265Notes

Reaction equation

HRID 1638265 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]1[N:12]1[C:16]([CH:17]=O)=[CH:15][N:14]=[CH:13]1.[CH2:20]([SH:23])[CH2:21][SH:22].Cl[Si](C)(C)C>ClCCl>[S:22]1[CH2:21][CH2:20][S:23][CH:17]1[C:16]1[N:12]([CH:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:10][CH2:11][C:2]2([CH3:19])[CH3:1])[CH:13]=[N:14][CH:15]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 109021,2-EthanedithiolHCID 20068366HCID 20068366, compound

Product 1

HCID 20068396HCID 20068396, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 5.1 parts of 1-(1,2,3,4-tetrahydro-2,2-dimethyl-1-naphthalenyl)-1H-imidazole-5-carboxaldehyde, 2.7 parts of 1,2-ethanethiol and 130 parts of dichloromethane were added dropwise 9.6 parts of chlorotrimethylsilane. Upon complete addition, stirring was continued overnight at 40° C. After cooling, the reaction mixture was washed with a potassium carbonate solution 10% in water and water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 3.69 parts (55.8%) of 5-(1,3-dithiolan-2-yl)-1-(1,2,3,4-tetrahydro-2,2-dimethyl-1-naphthalenyl)-1H-imidazole; mp. 109.3° C. (compound 2.52).

Workup

  1. additionUpon complete addition
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with a potassium carbonate solution 10% in water and water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from 2,2'-oxybispropane
  12. filtrationThe product was filtered off
  13. customdried

Sources & evidence

ORD record
ord-5f6e7f8e9c3541548799ef2a2564c0d3
Source dataset
uspto-grants-1989_11
Patent number
US04878940

Reaction notes

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