Phosphorus sulfide (P2S5) → HCID 86676949, compound

HRID 710092Notes

Reaction equation

HRID 710092 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][C:11]=2[F:20])=[C:4]([F:22])[CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:24]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[S:24])[C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][C:11]=2[F:20])=[C:4]([F:22])[CH:3]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 71257495HCID 71257495, compound

Product 1

HCID 86676949HCID 86676949, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Intermediate 32 (1 g, 2.56 mmol) dissolved in toluene (10 ml) and added P2S5 (0.57 g, 2.56 mmol). This mixture was refluxed for 18 h. Toluene removed on rotavapour to obtain the crude. Crude was purified by column chromatography on 60-120 mesh silicagel using EtOAc and Petether (20:80) as eluent to afford the title compound (500 mg) as a yellow solid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 11.02 (s, 1H), 7.92-7.85 (m, 2H), 7.69 (dd, J 1.6, 8.1, 1H), 7.63 (dd, J 1.6, 9, 1H), 7.33-7.27 (m, 2H), 3.02 (s, 3H).

Workup

  1. temperatureThis mixture was refluxed for 18 h
  2. customToluene removed on rotavapour
  3. customto obtain the crude
  4. customCrude was purified by column chromatography on 60-120 mesh silicagel

Sources & evidence

ORD record
ord-389dddae9f2c4311a3ccbf96a094982d
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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