Acetic Acid → HCID 19890937, compound

HRID 893631Notes

Reaction equation

HRID 893631 reaction equation
[C:1]([SeH])(=[Se:9])[C:2]1C(=C[CH:6]=[CH:7][CH:8]=1)O.[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+].Cl.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH2:34]Cl.Cl.[C:37]([OH:40])(=[O:39])[CH3:38]>O>[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH2:34][Se:9][C:1]1[CH:2]=[CH:8][CH:7]=[CH:6][C:38]=1[C:37]([OH:40])=[O:39]

Participants

9

Reactant 7

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 23392Picolyl chloride hydrochlorideHCID 24489Sodium DithioniteHCID 178515948HCID 178515948, compound

Product 1

HCID 19890937HCID 19890937, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred suspension of 10 g (0.025 mol) diselenosalicylic acid in 75 ml water is added 7.6 g (0.19 ml) sodium hydroxide, when the internal temperature rises slightly and the acid goes into solution. Then 20 g (0.189 mol) sodium carbonate and 11.6 g (0.067 mol) sodium dithionite are added with slight heating, followed by 2 h heating under reflux. After cooling to room temperature 9.8 g (0.06 mol) 2-picolyl chloride hydrochloride dissolved in 20 ml water are added dropwise and stirring is continued at room temperature for 14 h. Then 25% hydrochloric acid is added to adjust to pH 8 to 9 followed by acetic acid (98%) to pH 5-6. The precipitated white crude product is sucked off, washed neutral with water and recrystallized from 2-propanol (900 ml).

Workup

  1. temperatureheating
  2. temperatureunder reflux
  3. additionare added dropwise
  4. waitis continued at room temperature for 14 h
  5. washwashed neutral with water
  6. customrecrystallized from 2-propanol (900 ml)

Sources & evidence

ORD record
ord-009d59f47e724be48c07a6b08c2cb3a3
Source dataset
uspto-grants-1992_06
Patent number
US05126357

Reaction notes

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