Diboron → 1,4,10,13-Tetrathia-7,16-diazacyclooctadecane

HRID 1658910Notes

Reaction equation

HRID 1658910 reaction equation
B#B.O=[C:4]1[CH2:21][S:20][CH2:19][CH2:18][S:17][CH2:16][C:15](=O)[NH:14][CH2:13][CH2:12][S:11][CH2:10][CH2:9][S:8][CH2:7][CH2:6][NH:5]1>O1CCCC1>[S:8]1[CH2:9][CH2:10][S:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][S:17][CH2:18][CH2:19][S:20][CH2:21][CH2:4][NH:5][CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 6328200DiboronHCID 21316280HCID 21316280, compound

Product 1

HCID 5604941,4,10,13-Tetrathia-7,16-diazacyclooctadecane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diborane (20 ml.; 1.5 N) in anhydrous tetrahydrofuran is added dropwise to a suspension of 2 g. of the diamide obtained in Example 32 in 50 ml. anhydrous tetrahydrofurane under nitrogen at room temperature. The solid dissolves giving a clear solution. After the addition is completed the mixture is refluxed during four hours and a solid precipitate is formed. After cooling to room temperature, the excess reagent is destroyed by adding carefully 10 ml. of water. The solvents are evaporated to dryness and 6 N hydrochloric acid (50 ml.) is added to the solid residue. The mixture is refluxed for three hours: the solid does not dissolve, the mixture remaining heterogeneous. The mixture is evaporated to dryness and a solution of 10% sodium hydroxide in water (50 ml.) is added to the residue.

Workup

  1. customat room temperature
  2. dissolutionThe solid dissolves
  3. customgiving a clear solution
  4. additionAfter the addition
  5. temperatureis refluxed during four hours
  6. customa solid precipitate is formed
  7. customthe excess reagent is destroyed
  8. additionby adding carefully 10 ml
  9. customThe solvents are evaporated to dryness and 6 N hydrochloric acid (50 ml.)
  10. additionis added to the solid residue
  11. temperatureThe mixture is refluxed for three hours
  12. dissolutionthe solid does not dissolve
  13. customThe mixture is evaporated to dryness
  14. additiona solution of 10% sodium hydroxide in water (50 ml.) is added to the residue

Sources & evidence

ORD record
ord-7641a9710c064a129cfbc091973b6f50
Source dataset
uspto-grants-1976_06
Patent number
US03966766

Reaction notes

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