1-Amidino-4,4-diethyl-2-oxoimidazolidine hydrobromide → HCID 178428592, compound

HRID 1898928Notes

Reaction equation

HRID 1898928 reaction equation
Br.[C:2]([N:5]1[CH2:9][C:8]([CH2:12]C)([CH2:10]C)[NH:7][C:6]1=[O:14])(=[NH:4])[NH2:3].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.[CH:37]1([CH2:40][N:41]([C:51]2[CH:56]=[CH:55][CH:54]=[C:53]([C:57]([F:60])([F:59])[F:58])[CH:52]=2)[C:42](=[O:50])[C:43]([C:48]#[N:49])=[CH:44]OCC)[CH2:39][CH2:38]1>>[C:48]([C:43]([C:42](=[O:50])[N:41]([CH2:40][CH:37]1[CH2:39][CH2:38]1)[C:51]1[CH:56]=[CH:55][CH:54]=[C:53]([C:57]([F:58])([F:60])[F:59])[CH:52]=1)=[CH:44][NH:3][C:2](=[NH:4])[N:5]1[CH2:9][C:8]([CH3:10])([CH3:12])[NH:7][C:6]1=[O:14])#[N:49]

Participants

4

Reactant 3

HCID 233728611-Amidino-4,4-diethyl-2-oxoimidazolidine hydrobromideHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-eneHCID 543416392-cyano-3-ethoxyacrylic acid N-cyclopropylmethyl-N-(3-trifluoromethylphenyl)amide

Product 1

HCID 178428592HCID 178428592, compoundYield 36.4%

Procedure

Starting from 6.58 g (24.8 mmol) of 1-amidino-4,4-diethyl-2-oxoimidazolidine hydrobromide (comp. III: R1, R2 =C2H5 ; R3 =H as hydrobromide) and 3.87 g (26.1 mmol) of diazabicycloundecene (DBU) as auxiliary base and 7.40 g (24.8 mmol) of a compound IV (R4 =CH3 ; R5, R6 =H; R7 =C3H5) by the procedure described in Examples 82-84, 3.94 g (=36.4% yield) of pure 1-cyano-1-[N-methyl-N-(3-trifluoromethylphenyl)carbamoyl]-2-[imino(4,4-diethyl-2-oxo-1-imidazolidinyl)methylamino]ethene (comp. II: R1, R2 =C2H5 ; R3, R5, R6 =H; R4 =CH3) were obtained, melting point 184°-87°.

Sources & evidence

ORD record
ord-e95aba98f6db42b4a8c21f14665131ff
Source dataset
uspto-grants-1996_11
Patent number
US05571816

Reaction notes

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