Dimethylformamide → HCID 13038091, compound

HRID 1759334Notes

Reaction equation

HRID 1759334 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(NC(C)C)(C)C.CN(C)C=O.[F:24][C:25]([F:29])=[C:26]([F:28])[F:27]>C(OCC)(=O)C.O>[F:24][C:25]([F:29])([S:11][C:8]1[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=1)[CH:26]([F:28])[F:27]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 8301TetrafluoroethyleneHCID 707774'-Mercaptoacetanilide

Product 1

HCID 13038091HCID 13038091, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 25 g (0.15 mole) of 4-acetamidothiophenol and 15 g (0.15 mole) of diisopropylamine in 80 of dimethylformamide was treated with 15 g (0.15 mole) of tetrafluoroethylene in a bomb. The temperature was slowly raised from -44° C. to 25° C. The reaction mixture was then poured into water and the solid product was isolated by filtration. The solid was dissolved in ethyl acetate and the resulting solution was dried over anhydrous magnesium sulfate, filtered, and concentrated. The solid residue was triturated with petroleum ether and filtered to give 35 g (87.5% yield) of p-(1,1,2,2-tetrafluoroethylthio)acetanilide (XI); m.p. 133.5°-135° C.

Workup

  1. temperatureThe temperature was slowly raised from -44° C. to 25° C
  2. customthe solid product was isolated by filtration
  3. dry with materialthe resulting solution was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe solid residue was triturated with petroleum ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-8a5fea2e5f5045ac863ede26f554cb12
Source dataset
uspto-grants-1982_07
Patent number
US04340606

Reaction notes

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