Isocyanic acid → 2,5-Dimethyl-3,6-dihexyl-pyrazine

HRID 267658

Reaction equation

HRID 267658 reaction equation
[N:1](=[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:4](=O)[CH3:5])O.[CH3:13][C:14](=O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[N:23](Cl)=O.N=C=O>[Zn].C(O)(=O)C>[CH3:13][C:14]1[C:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[N:23][C:4]([CH3:5])=[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[N:1]=1

Participants

7

Reactant 4

HCID 6347Isocyanic acidHCID 131872-NonanoneHCID 17601Nitrosyl chlorideHCID 736826343-Oximino-2-nonanone

Product 1

HCID 218149392,5-Dimethyl-3,6-dihexyl-pyrazine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

h. 2,5-Dimethyl-3,6-dihexyl-pyrazine was prepared by first forming 3-oximino-2-nonanone by reacting 2-nonanone 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-dihexyl-pyrazine which had a b.p. of 112°-120°C./0.01 mm. Hg.

Sources & evidence

ORD record
ord-aac9aaea7a43424d8d4d18380ddd96d4
Source dataset
uspto-grants-1976_03
Patent number
US03943260

Linked notes

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