Isocyanic acid → 2,5-Dimethyl-3,6-di(propan-2-yl)pyrazine

HRID 1606204

Reaction equation

HRID 1606204 reaction equation
[CH3:1][CH:2]([CH3:9])[C:3](=[N:7]O)[C:4](=O)[CH3:5].[CH3:10][CH:11]([CH3:16])[CH2:12][C:13](=O)[CH3:14].[N:17](Cl)=O.N=C=O>[Zn].C(O)(=O)C>[CH3:5][C:4]1[C:3]([CH:2]([CH3:9])[CH3:1])=[N:7][C:13]([CH3:14])=[C:12]([CH:11]([CH3:16])[CH3:10])[N:17]=1

Participants

7

Reactant 4

HCID 6347Isocyanic acidHCID 7909Methyl Isobutyl KetoneHCID 17601Nitrosyl chlorideHCID 67951124-Methyl-3-oximino-2-pentanone

Product 1

HCID 133209922,5-Dimethyl-3,6-di(propan-2-yl)pyrazine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

d. 2,5-Dimethyl-3,6-diisopropyl-pyrazine was prepared by first forming 4-methyl-3-oximino-2-pentanone by reacting 4-methyl-2-pentanone with nitrosyl chloride according to the method of Bouveault, Bull. [3] 31, 1163 (1904). 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-diisopropyl-pyrazine which had a b.p. of 91°C./8 mm. Hg.

Sources & evidence

ORD record
ord-47983119b91f4278a34084ba47ead6ed
Source dataset
uspto-grants-1976_04
Patent number
US03952026

Linked notes

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