Water → HCID 10926323, compound

HRID 861834Notes

Reaction equation

HRID 861834 reaction equation
[C:1]([C:3]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5])#[N:2].[H-].[Na+].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.O>CN(C=O)C>[C:1]([C:3]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([O:8][S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:25])=[O:24])[C:4]([F:7])([F:5])[F:6])#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 46073381-Cyano-1-phenyl-2,2,2-trifluoroethanol

Product 1

HCID 10926323HCID 10926323, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.2 g (25 mmol) of 1-cyano-2,2,2-trifluoro-1-phenyl-ethanol were dissolved in 50 ml of DMF, and 0.9 g (30 mmol) of sodium hydride (80% strength dispersion in mineral oil) was added. 5.5 g (29 mmol) of toluene-4-sulfonyl chloride were added in portions to the virtually clear solution after about 1 hour. The mixture was stirred for 8 hours, allowed to stand overnight and then poured into water. The oily liquid which separated out solidified on cooling. The solid was filtered off with suction and dried. 6.3 g of 1-cyano-1-phenyl-1-(toluene-4-sulfonyloxy)-2,2,2-trifluoroethane were obtained (colorless crystals, m.p.: 70° C. [from ligroin]).

Workup

  1. waitto stand overnight
  2. customThe oily liquid which separated out
  3. temperatureon cooling
  4. filtrationThe solid was filtered off with suction
  5. customdried

Sources & evidence

ORD record
ord-962f3032faf84c1781f0bdfcdb16e8ab
Source dataset
uspto-grants-1998_02
Patent number
US05716756

Reaction notes

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