Isocyanic acid → 3,6-Dipentyl-2,5-dimethylpyrazine

HRID 1606189

Reaction equation

HRID 1606189 reaction equation
[N:1](=[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:4](=O)[CH3:5])O.[CH3:12][C:13](=O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[N:21](Cl)=O.N=C=O>[Zn].C(O)(=O)C>[CH3:12][C:13]1[C:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[N:21][C:4]([CH3:5])=[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[N:1]=1

Participants

7

Reactant 4

HCID 6347Isocyanic acidHCID 80932-OctanoneHCID 17601Nitrosyl chlorideHCID 67981593-Oximino-2-octanone

Product 1

HCID 6059713,6-Dipentyl-2,5-dimethylpyrazine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

2,5-Dimethyl-3,6-diamyl-pyrazine was prepared by first forming 3-oximino-2-octanone by reacting 2-octanone 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-diamyl-pyrazine which had a b.p. of 78°C./0.03 mm. Hg.

Sources & evidence

ORD record
ord-2c7297cdcaab43e9bf4493b87d4cf232
Source dataset
uspto-grants-1976_04
Patent number
US03952024

Linked notes

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