Water → 1,4-Dioxa-10,13-dithia-7,16-diazacyclooctadecane

HRID 1658909Notes

Reaction equation

HRID 1658909 reaction equation
O=[C:2]1[NH:19][CH2:18][CH2:17][S:16][CH2:15][CH2:14][S:13][CH2:12][CH2:11][NH:10][C:9](=O)[CH2:8][O:7][CH2:6][CH2:5][O:4][CH2:3]1.B#B.O>O1CCCC1>[O:4]1[CH2:5][CH2:6][O:7][CH2:8][CH2:9][NH:10][CH2:11][CH2:12][S:13][CH2:14][CH2:15][S:16][CH2:17][CH2:18][NH:19][CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 6328200DiboronHCID 21316276HCID 21316276, compound

Product 1

HCID 153217441,4-Dioxa-10,13-dithia-7,16-diazacyclooctadecane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 7 g. of the cyclic diamide obtained in Example 28 in 100 ml. anhydrous tetrahydrofurane is added slowly to 50 ml. of a freshly prepared solution (1.5 M) of diborane in anhydrous tetrahydrofuran under nitrogen atmosphere and at a temperature of 0°C. The mixture is then heated to reflux for two hours. The excess reagent is destroyed by adding 10 ml. of water and the solution is evaporated to dryness on a rotatary evaporator under vacuum. 100 ml. 6N hydrochloric acid are added to the residue and the mixture is refluxed for two hours; a clear solution is obtained. This solution is then evaporated to dryness under vacuum. The residue is dissolved in 30 ml. water and the solution is pressed 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 combined water solutions obtained are evaporated to dryness under vacuum on a water bath (80°C - 100°C). The residue is recrystallized.

Workup

  1. customat a temperature of 0°C
  2. temperatureThe mixture is then heated
  3. temperatureto reflux for two hours
  4. customThe excess reagent is destroyed
  5. additionby adding 10 ml
  6. customof water and the solution is evaporated to dryness on a rotatary evaporator under vacuum
  7. addition6N hydrochloric acid are added to the residue
  8. temperaturethe mixture is refluxed for two hours
  9. customa clear solution is obtained
  10. customThis solution is then evaporated to dryness under vacuum
  11. dissolutionThe residue is dissolved in 30 ml
  12. washThe column is washed with water until there
  13. customno basic reaction
  14. customare evaporated to dryness under vacuum on a water bath (80°C - 100°C)
  15. customThe residue is recrystallized

Sources & evidence

ORD record
ord-59910e6f1ffe4cc5a4bedbd6fff51b98
Source dataset
uspto-grants-1976_06
Patent number
US03966766

Reaction notes

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