Diphosgene → HCID 23110306, compound

HRID 2356931Notes

Reaction equation

[O:1]=[C:2](Cl)OC(Cl)(Cl)Cl.[N+:9]([C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[O:19][C:20]([F:23])([F:22])[F:21])[NH2:15])([O-:11])=[O:10].CO[C:26](=[O:38])[C:27]([CH3:37])([NH:29][CH2:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1)[CH3:28]>ClCCCl.C1COCC1>[CH3:37][C:27]1([CH3:28])[N:29]([CH2:30][C:31]2[CH:32]=[CH:33][N:34]=[CH:35][CH:36]=2)[C:2](=[O:1])[N:15]([C:14]2[CH:16]=[CH:17][C:18]([O:19][C:20]([F:21])([F:22])[F:23])=[C:12]([N+:9]([O-:11])=[O:10])[CH:13]=2)[C:26]1=[O:38]

Participants

Conditions

Temperature: 50 °C

Procedure

29 g (146.5 mmol) diphosgene in 300 ml 1,2-dichlorethane were treated at −20° C. with a solution of 13 g (58.6 mmol) 3-nitro-4-(trifluormethoxy)-aniline in 20 ml 1,2-dichlorethane. The mixture was allowed to come to room temperature and then was heated to 50° C. for 3 h. After standing over night, the solvent was evaporated and the residual oil was taken up in 250 ml THF. 13 g (58.6 mmol) 2-methyl-2-[(pyridin-4-ylmethyl)-amino]-propionic acid methyl ester in 250 ml THF were added and the mixture was heated to 40° C. for 1 h. The solvent was evaporated and the residue purified by flash chromatography (Silica gel, methylene chloride:methanol=95:5). Yield: 19.7 g.

Workup

customto come to room temperature
waitAfter standing over night
customthe solvent was evaporated
temperaturethe mixture was heated to 40° C. for 1 h
customThe solvent was evaporated
customthe residue purified by flash chromatography (Silica gel, methylene chloride:methanol=95:5)

Sources & evidence

ORD record: ord-38df5afa8d954ccfba6e0b8223518c69
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759379B2

Reaction notes

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