Hydrazine → HCID 178496297, compound

HRID 466041

Reaction equation

[NH2:1][NH2:2].[H-].[Na+].[CH3:5][C:6]([C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:16]=1[O:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])[C:12]#[N:13])([CH3:8])[CH3:7].C(=O)(O)[O-].[Na+]>O1CCCC1.O>[CH3:8][C:6]([C:9]1[CH:10]=[C:11]([C:12]([NH:1][NH2:2])=[NH:13])[CH:14]=[C:15]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:16]=1[O:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])([CH3:5])[CH3:7]

Participants

Conditions

Temperature: 0 °C

Procedure

97% anhydrous hydrazine (4.8 g, 0.151 mole) is added dropwise to a stirred 0° C. suspension of sodium hydride (2.8 g of a 60% dispersion in mineral oil, 0.071 mol) in tetrahydrofuran (70 m) under nitrogen. After 90 minutes, a solution of 3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]benzonitrile (6.7 g, 0.021 mole) in tetrahydrofuran (15 ml) is added dropwise. After stirring two hours at 0° C., water 2.4 ml) is added dropwise. The mixture is poured into cold, saturated aqueous sodium bicarbonate 20 ml). The product is extracted with a 1:1 ethyl acetate/ether mixture (60 ml). The organic layer is washed with saturated aqueous NaCl and dried over MgSO4. Filtration and concentration provided a solid which was recrystallized from ethyl acetate/hexane to give 4.9 g (7.3 g theor., 67%) of 3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]benzene carboximidic acid hydrazide, mp 133° C.

Workup

extractionThe product is extracted with a 1:1 ethyl acetate/ether mixture (60 ml)
washThe organic layer is washed with saturated aqueous NaCl
dry with materialdried over MgSO4
filtrationFiltration and concentration
customprovided a solid which
customwas recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record: ord-62dcd841198a4b69b96afab4839a93aa
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05155122

Linked notes

Loading…