Diboron → 4,7,13,16-Tetraoxa-21,24-dithia-1,10-diazabicyclo[8.8.8]hexacosane

HRID 263273Notes

Reaction equation

HRID 263273 reaction equation
O=[C:2]1[CH2:19][O:18][CH2:17][CH2:16][O:15][CH2:14][C:13](=O)[N:12]2[CH2:21][CH2:22][S:23][CH2:24][CH2:25][S:26][CH2:27][CH2:28][N:3]1[CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11]2.B#B>O1CCCC1>[N:3]12[CH2:28][CH2:27][S:26][CH2:25][CH2:24][S:23][CH2:22][CH2:21][N:12]([CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)[CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:2]2

Participants

4

Reactant 2

HCID 6328200DiboronHCID 21316305HCID 21316305, compound

Product 1

HCID 205569634,7,13,16-Tetraoxa-21,24-dithia-1,10-diazabicyclo[8.8.8]hexacosaneYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.6 g. of the bicyclic diamide obtained in Example 30 in 30 ml. anhydrous tetrahydrofuran is slowly added to 20 ml. of the fresh prepared diborane solution (1.5 N) under nitrogen atmosphere and a temperature of 0° C. The mixture is stirred two hours at reflux temperature. The excess reagent is destroyed by adding 5 ml. of water and the solution is evaporated on a rotary evaporator under vacuum. This residue is treated with 50 ml. 6 N hydrochloric acid under heating at reflux for two hours and a solution is obtained. The mixture is evaporated under vacuum on a rotary evaporator (water bath 80°-100° C.). The residue is dissolved in 50 ml. water and the solution is passed through a column of an anion exchange resin (Dowex 1, Trade Mark). The column is washed with water until there is no basic reaction. The water is evaporated. The residue is dried in vacuum (0.1 mm. Hg) and recrystallized from a benzene and heptane mixture, yielding the desired compound.

Workup

  1. customa temperature of 0° C
  2. temperatureat reflux temperature
  3. customThe excess reagent is destroyed
  4. additionby adding 5 ml
  5. customof water and the solution is evaporated on a rotary evaporator under vacuum
  6. additionThis residue is treated with 50 ml
  7. temperature6 N hydrochloric acid under heating
  8. temperatureat reflux for two hours
  9. customa solution is obtained
  10. customThe mixture is evaporated under vacuum on a rotary evaporator (water bath 80°-100° C.)
  11. dissolutionThe residue is dissolved in 50 ml
  12. washThe column is washed with water until there
  13. customno basic reaction
  14. customThe water is evaporated
  15. customThe residue is dried in vacuum (0.1 mm. Hg)
  16. customrecrystallized from a benzene and heptane mixture

Sources & evidence

ORD record
ord-9d2a80a3447342c0b054b8646df94d58
Source dataset
uspto-grants-1979_05
Patent number
US04156683

Reaction notes

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