Water → 2-(2-Nitrophenylthio)benzonitrile

HRID 1609276Notes

Reaction equation

HRID 1609276 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([NH2:15])=O)([O-:3])=[O:2].FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>N1C=CC=CC=1.O1CCOCC1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]#[N:15])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 27287042-(2-Nitrophenylthio)benzamide

Product 1

HCID 200844502-(2-Nitrophenylthio)benzonitrileYield 95.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Procedure

In a mixture of 12.7 g of pyridine and 80 ml of dioxane was suspended 8.8 g of 2-(2-nitrophenylthio)benzamide, followed by dropwise addition of 10.1 g of trifluoroacetic anhydride with ice-cooling, and the mixture was stirred for 1 hour. To the reaction mixture was added water and the crystals separated out therefrom were collected by filtration, washed with water and hot ethanol and dried. The procedure gave 7.84 g of the title compound as yellow crystals, m.p. 166°-167° C.

Workup

  1. temperaturecooling
  2. customthe crystals separated out
  3. filtrationtherefrom were collected by filtration
  4. washwashed with water and hot ethanol
  5. customdried

Sources & evidence

ORD record
ord-e86f7034c7034214a35716b75b895a56
Source dataset
uspto-grants-1995_03
Patent number
US05399703

Reaction notes

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