Urea → HCID 46899385, compound

HRID 1897841Notes

Reaction equation

[NH2:1][C:2]1[C:6]([NH2:7])=[CH:5][S:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][CH:16]=[C:17]([NH2:20])[C:18]=2[NH2:19])=[CH:10][CH:9]=1.N[C:22](N)=[O:23].[CH2:25]([OH:30])CCCC>>[O:30]=[C:25]1[NH:20][C:17]2=[CH:16][S:15][C:14]([C:11]3[CH:10]=[CH:9][C:8]([C:3]4[S:4][CH:5]=[C:6]5[C:2]=4[NH:1][C:22](=[O:23])[NH:7]5)=[CH:13][CH:12]=3)=[C:18]2[NH:19]1

Participants

Reactant 3

HCID 1176Urea

HCID 62761-Pentanol

HCID 58399742HCID 58399742, compound

Product 1

HCID 46899385HCID 46899385, compound

Conditions

Temperature: 130 °C

Procedure

To the resulting 2-[4-(3,4-diaminothien-2-yl)phenyl]thiophene-3,4-diamine were added 2.2 equivalents of urea and amyl alcohol in an amount equivalent to 10 ml/mmol, and under argon gas atmosphere, a reaction was advanced by refluxing at 130° C. for 5 hours, then amyl alcohol was distilled off and the residue was purified by silica gel column chromatography using an ethyl acetate/hexane solvent, so that 4-[4-(2,3-dihydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)phenyl]-2,3-dihydro-1H-thieno[3,4-d]imidazol-2-one was obtained. The yield based on 2-[4-(3,4-diaminothien-2-yl)phenyl]thiophene-3,4-diamine was 60%.

Workup

distillationamyl alcohol was distilled off
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-8f634269bcc947de81b38aa39c6831bc
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08519150B2

Reaction notes

Loading…