Acetic Anhydride → HCID 20361754, compound

HRID 1580309Notes

Reaction equation

HRID 1580309 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:19])([C:14]1[NH:15][CH2:16][CH2:17][N:18]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:20](OC(=O)C)(=[O:22])[CH3:21]>O1CCOCC1>[C:20]([N:18]1[CH2:17][CH2:16][N:15]=[C:14]1[C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)([OH:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 54348592HCID 54348592, compound

Product 1

HCID 20361754HCID 20361754, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

Dissolve 12.8 g. of 2[(2-pyridyl)hydroxybenzyl] imidazoline in 25 ml. of dioxane and, with vigorous stirring, slowly add 2.4 ml. of acetic anhydride in a drop-wise fashion. After each 0.5 ml. addition warm the solution to 60° C for 5 min. and then cool the solution to 20° C before adding additional anhydride. Continue the stirring for 20 hours, filter the precipitated acetate salt and concentrate the resulting filtrate to about 10 mls. Recrystallize the desired product from alcohol to yield 1-acetyl-2[(2-pyridyl)-hydroxybenzyl]imidazoline, m.p. 150°-153° C.

Workup

  1. dissolutionDissolve 12.8 g
  2. additionaddition
  3. temperaturecool the solution to 20° C
  4. customstirring for 20 hours
  5. filtrationfilter the precipitated acetate salt
  6. concentrationconcentrate the resulting filtrate to about 10 mls
  7. customRecrystallize the desired product from alcohol

Sources & evidence

ORD record
ord-030bf9ecf4a24cd3b92971b6199e3506
Source dataset
uspto-grants-1976_01
Patent number
US03932431

Reaction notes

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