Acetic Anhydride → 5-Acetoxymethyl-2-phenyl-1H-imidazole

HRID 1075654Notes

Reaction equation

HRID 1075654 reaction equation
[OH:1][CH2:2][C:3]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][CH:4]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>C1(C)C=CC=CC=1>[C:14]([O:1][CH2:2][C:3]1[NH:7][C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:5][CH:4]=1)(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10080865(2-Phenyl-1H-imidazol-5-yl)methanol

Product 1

HCID 101767595-Acetoxymethyl-2-phenyl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
52.5 °C

Procedure

Mix 5-hydroxymethyl-2-phenyl-1H-imidazole (1.3 Kg) and toluene (10.4 L) at 20-25° C., and then heat the mixture with stirring to 50-55° C. Add acetic anhydride (780 ml, 1.1 equivalents) slowly and continue heating at 50-55° C. until the reaction is complete (typically 3-4 hours). Cool the reaction mixture to -5-0° C., filter off the product, wash it with toluene (3×700 ml) and then dry it under vacuum at 50-55° C. to constant weight.

Workup

  1. temperatureheat the mixture
  2. customtypically 3-4 hours
  3. temperatureCool the reaction mixture to -5-0° C.
  4. filtrationfilter off the product
  5. washwash it with toluene (3×700 ml)
  6. customdry it under vacuum at 50-55° C. to constant weight

Sources & evidence

ORD record
ord-d1071a8770eb4aa4a263369ae4bc67cc
Source dataset
uspto-grants-1999_05
Patent number
US05905152

Reaction notes

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