Diiodomethane → HCID 58500138, compound

HRID 1920271Notes

Reaction equation

C(ON=O)CC(C)C.I[CH2:10][I:11].[NH2:12][C:13]1[N:17]([CH2:18][CH2:19][O:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:16]([CH2:31][CH2:32][CH3:33])=[N:15][C:14]=1C#N>C(Cl)(Cl)Cl>[C:13]([C:14]1[N:15]=[C:16]([CH2:31][CH2:32][CH3:33])[N:17]([CH2:18][CH2:19][O:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[C:10]=1[I:11])#[N:12]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of isoamylnitrite (96 mL, 715 mmol), diiodomethane (475 mL), and chloroform (240 mL) was heated to 80° C. over a period of one hour. A solution of tert-butyl 2-[2-(5-amino-4-cyano-2-propyl-1H-imidazol-1-yl)ethoxy]ethylcarbamate (64.3 g, 191 mmol) in chloroform (240 mL) was added dropwise over a period of 115 minutes. During the addition the reaction temperature was decrease to 74° C. The reaction was allowed to cool to 50° C., and the chloroform was removed under reduced pressure. The resulting liquid was diluted with a small volume of dichloromethane and was purified by chromatography on silica gel (eluting sequentially with hexanes and ethyl acetate) and dried under high vacuum at 60° C. for eight hours to provide 56.3 g (66%) of tert-butyl 2-[2-(4-cyano-5-iodo-2-propyl-1H-imidazol-1-yl)ethoxy]ethylcarbamate as a dark orange oil containing a small amount of diiodomethane.

Workup

additionDuring the addition the reaction temperature
customto 74° C
customthe chloroform was removed under reduced pressure
additionThe resulting liquid was diluted with a small volume of dichloromethane
customwas purified by chromatography on silica gel (
washeluting sequentially with hexanes and ethyl acetate) and
customdried under high vacuum at 60° C. for eight hours

Sources & evidence

ORD record: ord-894404307dc248a8871357c598654edb
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168802B2

Reaction notes

Loading…