Water → (5-Diphenylphosphoryloxyimino-5H-thiophen-2-ylidene)-(2-methy1phenyl)-acetonitrile

HRID 1018892Notes

Reaction equation

HRID 1018892 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.[C:18]1([P:24](Cl)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.O>C1COCC1>[C:18]1([P:24]([O:1][N:2]=[C:3]2[S:7][C:6](=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[CH3:17])[C:9]#[N:10])[CH:5]=[CH:4]2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:25])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 73910Diphenylphosphinic chlorideHCID 86758612HCID 86758612, compound

Product 1

HCID 72652075(5-Diphenylphosphoryloxyimino-5H-thiophen-2-ylidene)-(2-methy1phenyl)-acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

4.7 g (20 mmol) of (5-Hydroxyimino-5H-thiophen-2-ylidene)-(2-methylphenyl)-acetonitrile, prepared as described in example 7.1, are dissolved in 50 ml of THF and cooled in an ice bath. After adding 5.1 g (21 mmol) of diphenylphosphinic chloride to the solution, 3.0 g (29 mmol) of triethylamine are added dropwise, keeping the temperature below 5° C. The reaction mixture is stirred at 5° C. for 30 min. The reaction mixture is poured into 50 ml of water, and filtered off. The yellow solid is washed with 50 ml of water and 50 ml of a mixture of water and CH3OH (10:1). The product is purified by the recrystallization from 2-PrOH to afford a yellow solid, mp 165-167° C.(Dec). The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 2.31 (s, 3H), 6.09 (d, 1H), 6.82 (d, 1H), 7.12-7.35 (m, 4H), 7.48-7.65 (m, 6H), 7.95-8.04 (m, 4H).

Workup

  1. temperaturecooled in an ice bath
  2. additionare added dropwise
  3. customthe temperature below 5° C
  4. filtrationfiltered off
  5. washThe yellow solid is washed with 50 ml of water and 50 ml of a mixture of water and CH3OH (10:1)
  6. customThe product is purified by the recrystallization from 2-PrOH
  7. customto afford a yellow solid, mp 165-167° C.(Dec)

Sources & evidence

ORD record
ord-53273702a41e42618761f373dd390c17
Source dataset
uspto-grants-2002_11
Patent number
US06485886B1

Reaction notes

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