Dimethyl Sulfoxide → HCID 13769698, compound

HRID 979935Notes

Reaction equation

HRID 979935 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH:16][CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][OH:25])[CH2:19][CH2:18]1.CS(C)=O.[H-].[Na+].Br[C:33]1[S:34][CH:35]=[CH:36][N:37]=1>O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH:16][CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][O:25][C:33]2[S:34][CH:35]=[CH:36][N:37]=2)[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 764302-BromothiazoleHCID 13588082HCID 13588082, compound

Product 1

HCID 13769698HCID 13769698, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 5.1 parts of 4-[[1-(2-furanylmethyl)-1H-benzimidazol-2-yl]amino]-1-piperidineethanol and 100 parts of dimethyl sulfoxide were added portionwise 0.9 parts of a sodium hydride dispersion 50%. After stirring for 1 hour at room temperature, 2.5 parts of 2-bromothiazole were added dropwise. Upon completion, stirring was continued overnight at room temperature. Water was added and the product was extracted twice with trichloromethane. The combined extracts were dried, filtered and evaporated. The residue was taken up in 4-methyl-2-pentanone. The organic phase was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from methylbenzene, yielding 0.3 parts of 1-(2-furanylmethyl)-N-[1-[2-(2-thiazolyloxy)ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 136.4° C. (compound 71).

Workup

  1. stirringUpon completion, stirring
  2. waitwas continued overnight at room temperature
  3. extractionthe product was extracted twice with trichloromethane
  4. customThe combined extracts were dried
  5. filtrationfiltered
  6. customevaporated
  7. washThe organic phase was washed with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by column chromatography over silica gel using
  12. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  13. customThe pure fractions were collected
  14. customthe eluent was evaporated
  15. customThe residue was crystallized from methylbenzene

Sources & evidence

ORD record
ord-481a44b6266c49c995c0486a9622bfc3
Source dataset
uspto-grants-1987_01
Patent number
US04634704

Reaction notes

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