Methyl iodide → HCID 12799321, compound

HRID 1262806Notes

Reaction equation

HRID 1262806 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([C:7]2[C:12]([NH2:13])=[N:11][C:10]([N:14]([CH3:16])[CH3:15])=[C:9]([Cl:17])[N:8]=2)[O:4][N:3]=1.[I:18][CH3:19].[Cl-].[Cl-].[Ca+2]>CN(C)C=O>[I-:18].[CH3:19][N+:3]1[O:4][C:5]([C:7]2[C:12]([NH2:13])=[N:11][C:10]([N:14]([CH3:15])[CH3:16])=[C:9]([Cl:17])[N:8]=2)=[N:6][C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 5284359Calcium ChlorideHCID 12799320HCID 12799320, compound

Product 1

HCID 12799321HCID 12799321, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2 ml of dry dimethylformamide is added 340 mg (1.33 mmole) of 3-amino-5-(3-amino-5-dimethylamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole. The resulting yellow solution is treated with 4 ml (64.3 mmole) of iodomethane. The homogeneous reaction mixture is protected from moisture (CaCl2) and allowed to stand at 40° C. overnight. The reaction mixture is cooled to room temperature and filtered to collect the solid which precipitated during the course of the reaction. The solid is washed with ether and air dried to afford 470 mg. (86%) of the title compound in pure form; m.p. 300°. The title compound can be further purified, if desired, by recrystallization from ethanol to give fine, yellow needles.

Workup

  1. filtrationfiltered
  2. customto collect the solid which
  3. customprecipitated during the course of the reaction
  4. washThe solid is washed with ether and air
  5. customdried
  6. customto afford 470 mg

Sources & evidence

ORD record
ord-3e2f29d845ae4f8ab3bb38e0c5b3161a
Source dataset
uspto-grants-1984_06
Patent number
US04454132

Reaction notes

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