2-Chlorophenothiazine → HCID 22027778, compound

HRID 1791116Notes

Reaction equation

HRID 1791116 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

4

Reactant 2

HCID 70882-ChlorophenothiazineHCID 10426Diphosgene

Product 1

HCID 22027778HCID 22027778, compoundYield 152.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

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

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

Sources & evidence

ORD record
ord-a4077a8ec4144f13941b8af582ce50fa
Source dataset
uspto-grants-2006_07
Patent number
US07074782B2

Reaction notes

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