Water → (5-Diethoxythiophosphoryloxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl)-acetonitrile

HRID 1018890Notes

Reaction equation

HRID 1018890 reaction equation
[OH:1][N:2]=[C:3]1[S:7][C:6](=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[C:9]#[N:10])[CH:5]=[CH:4]1.[P:18](Cl)([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[S:19].C(N(CC)CC)C.O>C1COCC1>[CH2:21]([O:20][P:18]([O:1][N:2]=[C:3]1[S:7][C:6](=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[C:9]#[N:10])[CH:5]=[CH:4]1)([O:23][CH2:24][CH3:25])=[S:19])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 17305O,O-diethyl phosphorochloridothioateHCID 86758612HCID 86758612, compound

Product 1

HCID 54211158(5-Diethoxythiophosphoryloxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl)-acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

8 g (33 mmol) of (5-Hydroxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl)-acetonitrile, prepared as described in example 7.1, are dissolved in 90 ml of THF and cooled in an ice bath. After adding 6.9 g (36 mmol) of diethyl chlorothiophosphate to the solution, 5.0 g (50 mmol) of triethylamine are added dropwise, keeping the temperature below 50° C. The reaction mixture is stirred at 50° C. for 60 min, then is poured into 100 ml of water, and extracted with ethyl acetate. The organic phase is washed with 0.1N hydrochloric acid solution, water, and sodium chloride solution. The organic phase is dried over MgSO4, the solvent is distilled off, and the residue is purified by a recrystallization from 2-PrOH. The product is obtained in the form of a brown solid, melting point 86-87° C. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 1.41 (t, 6H), 2.37 (s, 3H), 4.35-4.46 (m, 4H), 6.13 (d, 1H), 6.85 (d, 1H), 7.19-7.38 (m, 4H).

Workup

  1. temperaturecooled in an ice bath
  2. additionare added dropwise
  3. customthe temperature below 50° C
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed with 0.1N hydrochloric acid solution, water, and sodium chloride solution
  6. dry with materialThe organic phase is dried over MgSO4
  7. distillationthe solvent is distilled off
  8. customthe residue is purified by a recrystallization from 2-PrOH
  9. customThe product is obtained in the form of a brown solid, melting point 86-87° C

Sources & evidence

ORD record
ord-58871eb8ec65494d8f1d1796c104874c
Source dataset
uspto-grants-2002_11
Patent number
US06485886B1

Reaction notes

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