Ethyl xanthate → HCID 19876591, compound

HRID 1885977Notes

Reaction equation

HRID 1885977 reaction equation
[CH2:1]([O:3][C:4]([SH:6])=[S:5])[CH3:2].[K].[C:8]([C:11]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=1[N+]#N)([OH:10])=[O:9].[B-](F)(F)(F)F>CC(C)=O>[Cl:17][C:16]1[C:11]([C:8]([OH:10])=[O:9])=[C:12]([S:5][C:4]([O:3][CH2:1][CH3:2])=[S:6])[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 8823Ethyl xanthateHCID 26255TetrafluoroborateHCID 5462222PotassiumHCID 15059421HCID 15059421, compound

Product 1

HCID 19876591HCID 19876591, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a stirred suspension of 2.4 grams (0.014 mole) of ethylxanthic acid, potassium salt in 30 mL of acetone was added, by pipette, a stirred suspension of 2.0 grams (0.007 mole) of 2-carboxy-3-chlorobenzenediazonium tetrafluoborate in 50 mL of acetone. The flask containing the fluoborate suspension was rinsed with 20 mL of acetone, and the rinse was added to the reaction mixture. Upon completion of addition which required 7 minutes, the reaction mixture was stirred for about 18 hours. The reaction mixture was filtered to collect 2.0 grams of 6-chloro-2-[ethoxy(thiocarbonyl)thio]benzoic acid. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionwas added, by pipette
  2. washwas rinsed with 20 mL of acetone
  3. additionthe rinse was added to the reaction mixture
  4. additionUpon completion of addition which required 7 minutes
  5. filtrationThe reaction mixture was filtered
  6. customto collect 2.0 grams of 6-chloro-2-[ethoxy(thiocarbonyl)thio]benzoic acid

Sources & evidence

ORD record
ord-e4a02d485eee4678bd9bd9ba28dd128f
Source dataset
uspto-grants-1992_09
Patent number
US05149357

Reaction notes

Loading…