2-Pyrazinecarboxylic acid → N'-t-butyl-N-(pyrazinecarbonyl)-N'benzoylhydrazine

HRID 21653Notes

Reaction equation

C(N(CC)CC)C.[C:8]([N:12]([C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH2:13])([CH3:11])([CH3:10])[CH3:9].[N:22]1[CH:27]=[CH:26][N:25]=[CH:24][C:23]=1[C:28](O)=[O:29].CS(Cl)(=O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:8]([N:12]([C:14](=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[NH:13][C:28]([C:23]1[CH:24]=[N:25][CH:26]=[CH:27][N:22]=1)=[O:29])([CH3:11])([CH3:9])[CH3:10]

Participants

Conditions

Temperature: 23 °C

Procedure

Triethylamine (1.0 g, 0.01 mol) was added to a solution of N'-t-butyl-N'-benzoylhydrazine (0.86 g, 0.0031 mol) and pyrazine carboxylic acid (0.56 g, 0.0045 mol) in 10 ml of methylene chloride at 23° C. This mixture was added to a solution of methanesulfonyl chloride (0.6 g, 0.0052 mol) in 10 ml of methylene chloride at 0° C. The mixture was stirred at 23° C. for 3 hours and then allowed to stand at 23° C. overnight. Aqueous sodium bicarbonate was added and the layers were separated. The organic extracts were evaporated to give crude product which was triturated with ether to afford N'-t-butyl-N-(pyrazinecarbonyl)-N'-benzoylhydrazine as a white solid: m.p. 181°-183° C.

Workup

waitto stand at 23° C. overnight
customthe layers were separated
customThe organic extracts were evaporated
customto give crude product which
customwas triturated with ether

Sources & evidence

ORD record: ord-ec7670aeb74047e3932a8754f3a46ae4
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05424333

Reaction notes

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