Phosphorus pentachloride → HCID 57695508, compound

HRID 2079849Notes

Reaction equation

HRID 2079849 reaction equation
[CH2:1]([O:8][C:9]1[CH:22]=[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:20]([Br:31])=[CH:19][C:10]=1[C:11]([NH:13][CH2:14][CH2:15][CH2:16][O:17][CH3:18])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[Si]([N:42]=[N+:43]=[N-:44])(C)(C)C>ClCCl>[CH2:1]([O:8][C:9]1[CH:22]=[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:20]([Br:31])=[CH:19][C:10]=1[C:11]1[N:13]([CH2:14][CH2:15][CH2:16][O:17][CH3:18])[N:44]=[N:43][N:42]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 78378AzidotrimethylsilaneHCID 57695546HCID 57695546, compound

Product 1

HCID 57695508HCID 57695508, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,4-Bis-benzyloxy-5-bromo-N-(3-methoxy-propyl)-benzamide (3.3 g, 6.8 mmole) was dissolved in anhydrous dichloromethane (20 ml), then PCl5 (1.77 g, 8.2 mmol) was added and the resulting solution was stirred at r.t. for 3 h under nitrogen. The reaction mixture was then cooled to 0° C., and TMSN3 (6 ml, neat) was added at 0° C. and the resulting mixture was stirred at r.t. for 3 hr. After quenching the reaction with NaHCO3 solution, and the reaction mixture was extracted with dichloromethane (30 ml×3). The combined organic was dried over Na2SO4. After filtration and concentration, the residue was purified by flash chromatography on silica gel to give 5-(2,4-bis-benzyloxy-5-bromo-phenyl)-1-(3-methoxy-propyl)-1H-tetrazole (2.8 g, 82%). M.p.: 92-93° C.; 400 MHz 1H NMR (CDCl3) δ: 7.68 (s, 1H), 7.44-7.31 (m, 8H), 7.19-7.15 (m, 2H), 6.64 (s, 1H), 5.17 (s, 2H), 4.99 (s, 2H), 4.28 (t, J=7.2 Hz, 2H), 3.22 (t, J=6.0 Hz, 2H), 3.16 (s, 3H), 2.03 (pent, J=6.4 Hz, 2H); LCMS: 509, 511 [M+H].

Workup

  1. temperatureThe reaction mixture was then cooled to 0° C.
  2. stirringthe resulting mixture was stirred at r.t. for 3 hr
  3. customAfter quenching
  4. customthe reaction with NaHCO3 solution
  5. extractionthe reaction mixture was extracted with dichloromethane (30 ml×3)
  6. dry with materialThe combined organic was dried over Na2SO4
  7. filtrationAfter filtration and concentration
  8. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-105da8634e11405396198cae9196589c
Source dataset
uspto-grants-2011_04
Patent number
US07932279B2

Reaction notes

Loading…