Dabco → 2-Trifluoromethylvinyl 4-aminophenyl sulfone

HRID 267594Notes

Reaction equation

HRID 267594 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](I)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=O)C.[F:15][C:16]([F:20])([F:19])[CH:17]=[CH2:18].C(OP(Cl)(=O)[O-])C.N12CCN(CC1)CC2>CC(C)=O>[NH2:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([CH:18]=[CH:17][C:16]([F:20])([F:19])[F:15])(=[O:12])=[O:13])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 9237DabcoHCID 126723,3,3-TrifluoropropeneHCID 215551994-Acetamidobenzenesulfonyl iodideHCID 86592542Ethyl chlorophosphate

Product 1

HCID 537126712-Trifluoromethylvinyl 4-aminophenyl sulfone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent4×

Procedure

2-trifluoromethylvinyl 4-aminophenyl sulfone is prepared by the addition of 4-acetamidobenzenesulfonyl iodide to 1,1,1-trifluoropropene followed by dehydrohalogenation and removal of the N-acetyl protective group by hydrolysis in a hydrochloric acid-ethanol mixture. The product is dissolved in acetone (25.1 g or 0.1 mol), an acetone solution of 0.1 mol (17.3 g) of ethylphosphorochloridate in acetone added, followed by 11.2 g of 1,4-diazabicyclo[2.2.2]octane in 10% acetone solution. The reaction mixture is stirred for one hour at room temperature, filtered, most of the acetone evaporated, and the residue is mixed with chloroform, washed and worked up. There is thus obtained 4-diethoxyphosphoramidophenyl 2-trifluoromethylvinyl sulfone: ##SPC59##

Workup

  1. customfollowed by dehydrohalogenation and removal of the N-acetyl protective group by hydrolysis in a hydrochloric acid-ethanol mixture
  2. filtrationfiltered, most of the acetone
  3. customevaporated
  4. additionthe residue is mixed with chloroform
  5. washwashed

Sources & evidence

ORD record
ord-a5433ac917ed4d9a80f1c4a6191edc52
Source dataset
uspto-grants-1976_03
Patent number
US03943154

Reaction notes

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