4-Hydroxybenzyl Alcohol → HCID 86719586, compound

HRID 922601Notes

Reaction equation

HRID 922601 reaction equation
Cl[C:2]1[N:3]=[CH:4][NH:5][C:6]=1Cl.[OH:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]O)=[CH:11][CH:10]=1.[I:17][CH3:18]>>[I-:17].[OH:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][N:5]2[CH:6]=[CH:2][N+:3]([CH3:18])=[CH:4]2)=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 6328Methyl iodideHCID 1400184,5-Dichloroimidazole

Product 1

HCID 86719586HCID 86719586, compound

Conditions

Temperature
155 °C

Procedure

4,5-Dichloroimidazole (0.1 mol) and 4-hydroxybenzyl alcohol (0.1 mol) were combined and heated to 155° C. The crude product was washed with cold ethanol and recrystallized in an EtOH/DMF mixture. This powder (3-(4-hydroxybenzyl)-4,5-dichloroimidazole, 8.23 mmol) was then was dissolved in DMF (3 mL). Iodomethane (72.3 mmol) was added to the reaction mixture and refluxed for 24 hours at 80° C. The solvent was evaporated and remaining oil was washed using ethyl ether to yield a brown precipitate. Yield: 1.28 g, 61%. 1H NMR (300 MHz, DMSO-d6) 3.81 (3H, s, CH3N), 5.34 (2H, CH2), 6.82 (2H, d, Ar), 7.26 (2H, d, Ar), 9.32 (1H, s, NCHN), 9.70 (1H, s, OH).

Workup

  1. washThe crude product was washed with cold ethanol
  2. customrecrystallized in an EtOH/DMF mixture
  3. dissolutionThis powder (3-(4-hydroxybenzyl)-4,5-dichloroimidazole, 8.23 mmol) was then was dissolved in DMF (3 mL)
  4. temperaturerefluxed for 24 hours at 80° C
  5. customThe solvent was evaporated
  6. washwas washed
  7. customto yield a brown precipitate

Sources & evidence

ORD record
ord-3956ae4f0d4e48cf9cc36a04a5a93a4f
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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