Isocyanic acid → 2,5-Bis(2-methylpropyl)-3,6-dimethylpyrazine

HRID 1606188

Reaction equation

HRID 1606188 reaction equation
[CH3:1][CH:2]([CH3:10])[CH2:3][C:4](=[N:8]O)[C:5](=O)[CH3:6].[CH3:11][CH:12]([CH3:18])[CH2:13][CH2:14][C:15](=O)[CH3:16].[N:19](Cl)=O.N=C=O>[Zn].C(O)(=O)C>[CH3:6][C:5]1[C:4]([CH2:3][CH:2]([CH3:10])[CH3:1])=[N:8][C:15]([CH3:16])=[C:14]([CH2:13][CH:12]([CH3:18])[CH3:11])[N:19]=1

Participants

7

Reactant 4

HCID 6347Isocyanic acidHCID 80345-Methyl-2-hexanoneHCID 17601Nitrosyl chlorideHCID 714430275-Methyl-3-oximino-2-hexanone

Product 1

HCID 5854102,5-Bis(2-methylpropyl)-3,6-dimethylpyrazine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

2,5-Dimethyl-3,6-diisobutyl-pyrazine was prepared by first forming 5-methyl-3-oximino-2-hexanone by reacting 5-methyl-2-hexanone with nitrosyl chloride according to the method of BOUVEAULT (loc.cit.). The autocondensation of two moles of the imino-ketone in the presence of zinc and acetic acid [according to the method described in Chimia 11, 310 (1957)] yielded 2,5-dimethyl-3,6-diisobutyl-pyrazine which had a b.p. of 69°-70°C./0.01 mm. Hg.

Sources & evidence

ORD record
ord-fdad4f12461a470d9104689af1c872c1
Source dataset
uspto-grants-1976_04
Patent number
US03952024

Linked notes

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