1,3-Dibromo-2-propanol → HCID 86751509, compound

HRID 2293021Notes

Reaction equation

HRID 2293021 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][S:4](=[O:7])([OH:6])=[O:5].[OH-:11].[Na+].[C:13](=[O:16])([O-])[O-:14].[Na+].[Na+].Br[CH2:20][CH:21]([OH:24])[CH2:22]Br>O.C(O)C>[NH2:1][C@H:2]([C:13]([O:14][CH2:20][C:21]([O:9][C:8](=[O:10])[C@H:2]([CH2:3][S:4](=[O:6])([OH:7])=[O:5])[NH2:1])([OH:24])[CH3:22])=[O:16])[CH2:3][S:4](=[O:5])([OH:6])=[O:11]

Participants

7

Reactant 4

HCID 72871,3-Dibromo-2-propanol2×HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 72886L-Cysteic acid

Product 1

HCID 86751509HCID 86751509, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

24 g (0.128 mol) of cysteic acid is dissolved in 160 ml of water and 10.2 g (0.255 mol) of sodium hydroxide is added. After dissolution, 6.8 g (0.064) sodium carbonate is added, followed by 80 ml ethanol. While refluxing the solution, 16.8 g (0.077 mol) 1,3-dibromo-2-propanol is added gradually during a period of 4 hours, followed by refluxing overnight. An additional 16.8 g (0.077 mol) of 1,3-dibromo-2-propanol is added, followed by all-day reflux. The solution is distilled to remove solvents and the resulting solid which contains HPDC and other materials is recovered and triturated with methanol/water. The purified solid is triturated again with methanol only and stirred overnight to remove residual materials, followed by dissolution in 10 cc water. Adjustment of the solution pH to 3-5 precipitates out pure HPDC.

Workup

  1. additionis added
  2. additionis added gradually during a period of 4 hours
  3. temperatureby refluxing overnight
  4. waitfollowed by all-day
  5. temperaturereflux
  6. distillationThe solution is distilled
  7. customto remove solvents
  8. customis recovered
  9. customtriturated with methanol/water
  10. customThe purified solid is triturated again with methanol only
  11. customto remove residual materials
  12. dissolutionfollowed by dissolution in 10 cc water
  13. customAdjustment of the solution pH to 3-5 precipitates out pure HPDC

Sources & evidence

ORD record
ord-66386a6393ad46d6a272ca0e01b94a4b
Source dataset
uspto-grants-1997_11
Patent number
US05686402

Reaction notes

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