Sodium → 3,4-dihydro-2H-[1,3]oxazino[3,2-a]benzimidazole

HRID 2420308Notes

Reaction equation

HRID 2420308 reaction equation
[Na].CS(O)(=O)=O.O[CH2:8][CH2:9][CH2:10][N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[NH:13][C:12]1=[O:20]>C(O)C>[O:20]1[C:12]2=[N:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:11]2[CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 867353601,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one methanesulfonate

Product 1

HCID 110951143,4-dihydro-2H-[1,3]oxazino[3,2-a]benzimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.5 parts of sodium in 40 parts of absolute ethanol are added in the cold 5.4 parts of 1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one methansulfonate. The whole is stirred until all solid enters solution. The solution is further stirred and refluxed for 2 hours. After cooling, the reaction mixture is filtered from some inorganic matter and the filtrate is evaporated. The residue is dissolved in 80 parts of methylbenzene, boiled with activated charcoal, filtered and the filtrate is evaporated again. The solid residue is washed with cold methylbenzene and crystallized from 16 parts of methylbenzene, yielding 2.6 parts of 3,4-dihydro-2H-[1,3]oxazino[3,2-a]benzimidazole; mp. 116.5°-118.5° C.

Workup

  1. stirringThe solution is further stirred
  2. temperaturerefluxed for 2 hours
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture is filtered from some inorganic matter
  5. customthe filtrate is evaporated
  6. dissolutionThe residue is dissolved in 80 parts of methylbenzene
  7. filtrationfiltered
  8. customthe filtrate is evaporated again
  9. washThe solid residue is washed with cold methylbenzene
  10. customcrystallized from 16 parts of methylbenzene

Sources & evidence

ORD record
ord-7834f81d3feb45e3b327a0fecc2ecc63
Source dataset
uspto-grants-1978_08
Patent number
US04110333

Reaction notes

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