Phosphorus sulfide (P2S5) → HCID 178496617, compound

HRID 906685Notes

Reaction equation

HRID 906685 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([N:9]([CH3:21])[C:10]([C:12]2[CH:20]=[CH:19][C:15]3=[N:16][O:17][N:18]=[C:14]3[CH:13]=2)=O)[CH2:5][CH2:4]1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:23]>C1(C)C=CC=CC=1>[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([N:9]([CH3:21])[C:10]([C:12]2[CH:20]=[CH:19][C:15]3=[N:16][O:17][N:18]=[C:14]3[CH:13]=2)=[S:23])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 178496615HCID 178496615, compound

Product 1

HCID 178496617HCID 178496617, compoundYield 11.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-(trans-4-Methoxycyclohexyl)-N-methyl-[2,1,3]-benzoxadiazole-5-carboxamide (0.91 g, 3.2 is mmol) and phosphorus pentasulfide (1.42 g) were refluxed in toluene (40 ml) for 3 h. The mixture was cooled, filtered through a 2 cm layer of silica gel and washed with dichloromethane. Evaporation of the solvent and trituration with diethyl ether gave a yellow solid (0.11 g). Mp=137-138° C., 1H NMR (300 MHz, CDCl3, rotamers) δ 7.89-7.83 (m, 1H); 7.58-7.55 (m, 1H); 7.36-7.30 (m, 1H); 5.50-5.40 and 3.90-3.75 and 3.50-3.00 (m, 2H); 3.44 and 3.38 (s+s, 3H); 3.27 and 3.04 (s+s, 3H); 2.30-0.95 ppm (s, 8H).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through a 2 cm layer of silica gel
  3. washwashed with dichloromethane
  4. customEvaporation of the solvent and trituration with diethyl ether

Sources & evidence

ORD record
ord-38cdc5df74ed48f18f0797a3aaf9f329
Source dataset
uspto-grants-2011_09
Patent number
US08013003B2

Reaction notes

Loading…