2-Chlorophenothiazine → HCID 22027778, compound

HRID 2120118Notes

Reaction equation

[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1.[O:16]=[C:17]([Cl:23])OC(Cl)(Cl)Cl>C1(C)C(C)=CC=CC=1>[C:17]([Cl:23])(=[O:16])[NH2:5].[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a suspension of 2-chlorophenothiazine (2 g) in xylene (20 ml) was added diphosgene (3.4 g). The mixture was heated to 140° C. for 18 hrs. The mixture was then cooled and the xylene removed under reduced pressure. The residue was purified by flash chromatography (2-5% ethyl acetate/hexane) to afford the sub-title compound as a brown solid (2.04 g): 1H NMR (400 MHz, CDCl3) δ 7.26-7.43 (4H, m), 7.45-7.51 (1H, m), 7.59-7.68 (2H, m).

Workup

temperatureThe mixture was then cooled
customthe xylene removed under reduced pressure
customThe residue was purified by flash chromatography (2-5% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-c0f707cf12174bb4b27786fab7894170
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06689784B2

Reaction notes

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