Hydrazine → N,N',N",N"'-tetracyclohexylhydrazinedicarboximidamide

HRID 977513Notes

Reaction equation

[CH2:1]1[CH2:6][CH2:5][CH:4]([N:7]=[C:8]=[N:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:3][CH2:2]1.[NH2:16][NH2:17]>>[CH:10]1([NH:9][C:8]([NH:16][NH:17][C:8](=[N:7][CH:4]2[CH2:5][CH2:6][CH2:1][CH2:2][CH2:3]2)[NH:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:7][CH:4]2[CH2:3][CH2:2][CH2:1][CH2:6][CH2:5]2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

Reactant 2

HCID 9321Hydrazine

HCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 9933173N,N',N",N"'-tetracyclohexylhydrazinedicarboximidamide

Procedure

DCC (1.03 g, 4.97 mmol) was dissolved in tetrahydrofuran (15 mL). Hydrazine (135 mg, 4.22 mmol) was added via syringe. Stirring 30 hours at room temperature produced a clear yellow mixture which was evaporated to a white powder (922 mg). Solution of this powder in diethyl ether, filtration and acidification with HCl (60 mL of saturated Et2O) gave a yellow white precipitate (856 mg). Two recrystallizations (EtOH in an Et2O chamber) gave white prisms (133 mg, 18%, M.P. 288°-290° C.). The low percentage of nitrogen in the elemental analysis of this compound indicates that two equivalents of DCC have reacted to hydrazine, forming the title compound.

Sources & evidence

ORD record: ord-4c929213c3af40e98fe86bf90e082ef8
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05614630

Reaction notes

Loading…