Hydrochloric Acid → HCID 117666646, compound

HRID 1753670Notes

Reaction equation

HRID 1753670 reaction equation
[F:1][C:2]([F:9])([S:5]([O-:8])(=[O:7])=[O:6])[CH2:3]O.[CH2:10]([N+:17]([CH3:20])([CH3:19])[CH3:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.FC(F)(S([O-])(=O)=O)CO.C1([S+](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:49][CH2:50][CH2:51][CH2:52]C(Cl)=O.Cl>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[Cl:49][CH2:50][CH2:51][CH2:52][CH2:3][C:2]([F:9])([F:1])[S:5]([O-:8])(=[O:7])=[O:6].[CH2:10]([N+:17]([CH3:20])([CH3:19])[CH3:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 783704-Chlorobutyryl chlorideHCID 86632756Triphenylsulfonium 1,1-difluoro-2-hydroxyethanesulfonateHCID 87186540HCID 87186540, compound

Product 1

HCID 117666646HCID 117666646, compoundYield 78.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

In 60 g of methylene chloride were dissolved 16 g of benzyltrimethylammonium 1,1-difluoro-2-hydroxyethanesulfonate which had been prepared with reference to the synthesis of triphenylsulfonium 1,1-difluoro-2-hydroxyethanesulfonate described in JP-A 2009-258695 (U.S. Pat. No. 8,114,570), 7.6 g of triethylamine, and 0.6 g of 4-dimethylaminopyridine. Under ice cooling, a mixture of 8.5 g chlorobutyryl chloride and 20 g methylene chloride was added dropwise to this solution, followed by 4 hours of stirring. At the end of stirring, 50 g of 5 wt % dilute hydrochloric acid was added to quench the reaction. The organic layer was separated, washed with water, and concentrated in vacuum. To the concentrate, 100 g of MIBK was added. This was concentrated in vacuum again. The residue was washed with diisopropyl ether, obtaining 15 g of the target compound, benzyltrimethylammonium 2-(3-chloropropyl)-1,1-difluoroethanesulfonate as oily matter. Yield 74%.

Workup

  1. additionwas added dropwise to this solution
  2. stirringAt the end of stirring
  3. customto quench
  4. customthe reaction
  5. customThe organic layer was separated
  6. washwashed with water
  7. concentrationconcentrated in vacuum
  8. additionTo the concentrate, 100 g of MIBK was added
  9. concentrationThis was concentrated in vacuum again
  10. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-d48b341f5bc8418fa2a076d4da805ab0
Source dataset
uspto-grants-2015_10
Patent number
US09164384B2

Reaction notes

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