Acetyl chloride → HCID 19703103, compound

HRID 861410Notes

Reaction equation

HRID 861410 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[I:5][C:6]1[CH:15]=[CH:14][C:9]([C:10](=[N:12]O)[NH2:11])=[CH:8][CH:7]=1>N1C=CC=CC=1>[I:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]2[N:12]=[C:1]([CH3:2])[O:3][N:11]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 4429393N-Hydroxy-4-iodo-benzamidine

Product 1

HCID 19703103HCID 19703103, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetyl chloride (1.62 ml) was added to a solution of 4-iodobenzamidoxime (5.24 g) in pyridine (35 ml) at ambient temperature. The reaction mixture was heated at reflux for 3 hours. The mixture was cooled to ambient temperature, evaporated and ice-water was added to the residue. The solid was collected by filtration, washed with water and recrystallised from acetonitrile to give 3-(4-iodophenyl)-5-methyl-1,2,4-oxadiazole (4.43 g), m.p. 121°-122° C.; microanalysis found: C, 37.6; H, 2.4; N, 9.7%; C9H7IN2O requires: C, 37.8; H, 2.47; N, 9.79%; NMR: 2.66(3H,s), 7.77(2H,dd) and 7.94(2H,dd); m/z 287(M+H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. customevaporated
  4. additionice-water was added to the residue
  5. filtrationThe solid was collected by filtration
  6. washwashed with water
  7. customrecrystallised from acetonitrile

Sources & evidence

ORD record
ord-60e7dca7861b4cdd8438f9c508e13e25
Source dataset
uspto-grants-1998_02
Patent number
US05714496

Reaction notes

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