Water → HCID 86675068, compound

HRID 1509343Notes

Reaction equation

HRID 1509343 reaction equation
[OH:1][CH2:2][C:3]([F:9])([F:8])[S:4](Cl)(=[O:6])=[O:5].C(=O)([O-])O.[Na+].[OH:15][N:16]1[C:20](=[O:21])[CH2:19][CH2:18][C:17]1=[O:22].O>C(#N)C>[F:8][C:3]([F:9])([S:4]([O:15][N:16]1[C:20](=[O:21])[CH2:19][CH2:18][C:17]1=[O:22])(=[O:6])=[O:5])[CH2:2][OH:1]

Participants

6

Reactant 4

HCID 962WaterHCID 80170N-HydroxysuccinimideHCID 516892Sodium BicarbonateHCID 58288757HCID 58288757, compound

Product 1

HCID 86675068HCID 86675068, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

In 100 mL of acetonitrile, 25.5 g of a liquid of 2-hydroxy-1,1-difluoroethanesulfonyl chloride (purity: 98%, equivalent to 0.138 mol) was dissolved by stirring. The resulting solution was cooled to 0° C., admixed with 14.0 g (0.166 mol) of sodium hydrogencarbonate and 17.5 g (0.152 mol) of N-hydroxysuccinimide, and then, reacted at 0° C. for 24 hours. To the thus-obtained reaction solution, 125 mL of water was added. The reaction solution was subsequently extracted twice with 100 mL of ethyl acetate. The resulting organic layer was washed twice with 100 mL of water. The organic layer was further subjected to concentration and purified by distillation. With this, 20.7 g of the target compound was obtained as a colorless oily substance (yield: 52%, purity: 90%, pure content: 18.7 g).

Workup

  1. customreacted at 0° C. for 24 hours
  2. additionwas added
  3. extractionThe reaction solution was subsequently extracted twice with 100 mL of ethyl acetate
  4. washThe resulting organic layer was washed twice with 100 mL of water
  5. concentrationThe organic layer was further subjected to concentration
  6. distillationpurified by distillation

Sources & evidence

ORD record
ord-2b0bdd10b48147279ced1be23061c532
Source dataset
uspto-grants-2015_12
Patent number
US09221928B2

Reaction notes

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