Phosgene → HCID 18965182, compound

HRID 2226601Notes

Reaction equation

[CH:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[CH:9]=2)=[CH:3][CH:2]=1.[C:15](Cl)([Cl:17])=[O:16].CCCCCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[Br:14][C:10]1[CH:9]=[C:8]([N:7]([C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=2)[C:15]([Cl:17])=[O:16])[CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 15.0 g (60.4 mmole ) of 3-bromodiphenylamine [i.e., N-(3-bromophenyl)aniline][S. Kurzepa and J. Cieslak, Roczniki Chem., 34, 111 (1960)] in 30 ml of toluene and 50 ml (116 mmole) of 1.93M phosgene in toluene were combined and heated at 90° C. under nitrogen for 2 hours with stirring. The red-orange colored solution was cooled, flushed with nitrogen for 2 hours to remove excess phosgene and concentrated in vacuo to 18.0 g (58.0 mmole, 96%) of red-orange oil which was homogeneous by TLC (4:1 hexane-ethyl acetate, Rf =0.80).

Workup

temperatureThe red-orange colored solution was cooled
customflushed with nitrogen for 2 hours
customto remove excess phosgene

Sources & evidence

ORD record: ord-ae12763054c04ea081bacff9e61871c1
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05348955

Reaction notes

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