2-Chloroethanol → HCID 178478509, compound

HRID 365398Notes

Reaction equation

HRID 365398 reaction equation
[OH:1][C:2]1[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:30][CH2:31][CH2:32]O.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:30][CH2:31][CH2:32][O:1][C:2]1[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178515907HCID 178515907, compound

Product 1

HCID 178478509HCID 178478509, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
23 °C

Procedure

To a solution of 4-hydroxybenzimidazole (3.1 g, 32.4 mmol), triphenylphosphine (12.75 g, 48.6 mmol) and 2-chloroethanol (5.2 g, 64.8 mmol) in tetrahydrofuran (75 mL) at 0-5° C. was added over 30 min a solution of diethyl azodicarboxylate (8.5 g, 48.7 mmol) in tetrahydrofuran (75 mL). The mixture was warmed to 23° C. and stirred for 48 hr. The solvent was removed under vacuum to give a dark brown oil. Purification by chromatography (silica gel, ethyl acetate-1% 2M NH3 in methanol) afforded 2.9 g (63.8%) of a solid residue that was crystallized from ethyl acetate to give the title compound as a white solid, mp 153-154° C.

Workup

  1. customThe solvent was removed under vacuum
  2. customto give a dark brown oil
  3. customPurification by chromatography (silica gel, ethyl acetate-1% 2M NH3 in methanol)

Sources & evidence

ORD record
ord-f724ddae03ac4b0eba7056480177df4d
Source dataset
uspto-grants-2000_10
Patent number
US06127380

Reaction notes

Loading…