Water → HCID 86648108, compound

HRID 2061306Notes

Reaction equation

HRID 2061306 reaction equation
[CH:1]1([NH:7][C:8](=[O:10])[OH:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Na].[F:12][CH:13]([F:19])[CH2:14][S:15]([O-:18])(=[O:17])=[O:16].[Cl-].[C:21]1([S+:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>C(Cl)(Cl)Cl>[CH:1]1([NH:7][C:8](=[O:9])[OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:34]1([S+:27]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1.[F:12][CH:13]([F:19])[CH2:14][S:15]([O-:18])(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 61343Triphenylsulfonium chlorideHCID 86648109HCID 86648109, compound

Product 1

HCID 86648108HCID 86648108, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 300-mL reaction vessel was charged with 31.85 g (purity: 47%, 48.0 mmol) of sodium cyclohexylcarbamic acid-2,2-difluoroethylsulfonate, 15.8 g (52.9 mmol) of triphenylsulfonium chloride, 170 g of water and 30 g of chloroform. The resulting solution was stirred for 4 hours at room temperature and separated into two phases. The aqueous phase was extracted with chloroform. The thus-obtained organic phases were combined together. The combined organic phase faction was washed six times with water, subjected to concentration, washed three times with diisopropyl ether, and then, dried, thereby yielding 24.5 g of triphenylsulfonium cyclohexylcarbamic acid-2,2-difluoroethylsulfonate as a target product. The purity of the product was 76%; and the yield of the product was 70%.

Workup

  1. customA 300-mL reaction vessel
  2. customseparated into two phases
  3. extractionThe aqueous phase was extracted with chloroform
  4. washThe combined organic phase faction was washed six times with water
  5. concentrationsubjected to concentration
  6. washwashed three times with diisopropyl ether
  7. customdried

Sources & evidence

ORD record
ord-eb64b11c63fe47aa9deb860572d20034
Source dataset
uspto-grants-2012_10
Patent number
US08283106B2

Reaction notes

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