Isopropanol → HCID 178478079, compound

HRID 1028196Notes

Reaction equation

HRID 1028196 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([C:17]2[N:18]=[CH:19][N:20](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:21]=2)(O)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.CC(O)C.[OH-].[Na+]>I.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([C:17]2[N:18]=[CH:19][NH:20][CH:21]=2)=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 57437680HCID 57437680, compound2×

Product 1

HCID 178478079HCID 178478079, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 24841Hydrogen iodideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 1-(3 Chlorophenyl)-2-phenyl-l-(1-trityl-1H-imidazol-4-yl)ethanol, (Intermediate 15) mg; 0.9 mmol) in 57% aqueous HI (10 mL) and iPrOH (2 mL) was added red phosphorus (280 mg, 9.0 mmol) in a resealable tube was heated at 160° C. for 16 h. The mixture was then cooled to room temperature and poured into ice-water, which was then basified with NaOH and diluted with CHCl3. The residue was isolated in a typical aqueous workup using CHCl3 and purified by MPLC with 5 to 15% MeOH:.CH2Cl2 to give 4-(1-(3-chlorophenyl)-2-phenylvinyl)-1H-imidazole, as a solid, (86 rug), AGN-216677. 1HNMR (CD3OD, 300 MHz) δ 7.71 (s, 1H), 7.37-6.96 (m, 9H), 6.55 (s, 1H).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. customThe residue was isolated in a typical aqueous workup
  3. custompurified by MPLC with 5 to 15% MeOH

Sources & evidence

ORD record
ord-84c34e435176471aa44e01487eef6f29
Source dataset
uspto-grants-2014_05
Patent number
US08735438B2

Reaction notes

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