Acetic Anhydride → HCID 20531677, compound

HRID 1759327Notes

Reaction equation

HRID 1759327 reaction equation
[CH2:1]([N:8]1[C:12]([CH:13]=O)=[C:11]([Cl:15])[N:10]=[C:9]1[C:16]1[CH:21]=[CH:20][C:19]([N:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:26]O.C(OC(=O)C)(=O)C>N1C=CC=CC=1>[CH2:1]([N:8]1[C:12]([C:13]#[N:26])=[C:11]([Cl:15])[N:10]=[C:9]1[C:16]1[CH:21]=[CH:20][C:19]([N:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 443297Hydroxyamine hydrochlorideHCID 15099330HCID 15099330, compound

Product 1

HCID 20531677HCID 20531677, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

In 30 ml of pyridine were dissolved 3.4 g of 1-benzyl-4-chloro-2-(4-dimethylaminophenyl)-5-formylimidazole and 1.39 g of hydroxylamine hydrochloride, and 6 ml of acetic anhydride was added dropwise to the solution. After the addition was completed, the reaction solution was stirred at 100° C. for 3 hours, and evaporated to dryness under reduced pressure. The residue was dissolved in 100 ml of chloroform, washed with two 300 ml portions of water, and evaporated to dryness under reduced pressure. The residue was recrystallized twice from 30 ml of ethanol, yielding 2.1 g of 1-benzyl-4-chloro-2-(4-dimethylaminophenyl)-5-cyanoimidazole as slightly brown needles, m.p. 125°-127° C.

Workup

  1. additionwas added dropwise to the solution
  2. additionAfter the addition
  3. customevaporated to dryness under reduced pressure
  4. dissolutionThe residue was dissolved in 100 ml of chloroform
  5. washwashed with two 300 ml portions of water
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was recrystallized twice from 30 ml of ethanol

Sources & evidence

ORD record
ord-4f0b0c0bb1534d2d878d75fc85404314
Source dataset
uspto-grants-1982_07
Patent number
US04340598

Reaction notes

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