Potassium Carbonate → HCID 18185320, compound

HRID 1358768Notes

Reaction equation

HRID 1358768 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([NH:8][CH2:9][CH:10]([OH:13])[CH2:11]O)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[C:17]1[CH:22]=[CH:21][C:20]([S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])=[CH:19][C:18]=1[N+:30]([O-:32])=[O:31].[C:33](=[O:36])([O-])[O-].[K+].[K+]>C(#N)C.C(Cl)(Cl)Cl.C(O)(C)C>[N+:30]([C:18]1[CH:19]=[C:20]([S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])[CH:21]=[CH:22][C:17]=1[O:13][CH:10]([CH2:11][O:36][C:33]1[CH:22]=[CH:21][C:20]([S:23]([C:26]([F:29])([F:27])[F:28])(=[O:24])=[O:25])=[CH:19][C:18]=1[N+:30]([O-:32])=[O:31])[CH2:9][NH:8][C:7]1[CH:14]=[CH:15][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)([O-:32])=[O:31]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 15479561-Chloro-2-nitro-4-trifluoromethanesulfonylbenzeneHCID 18185350HCID 18185350, compound

Product 1

HCID 18185320HCID 18185320, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

A mixture of 3-(4-nitroanilino)-1,2-propanediol (71 mg, 0.33 mmol), 1-chloro-2-nitro-4-trifluoromethanesulfonyl-benzene (135 mg, 0.47 mmol) and potasium carbonate (190 mg, 1.33 mmol) in acetonitrile (2 mL) was heated to reflux for 2 days. The reaction was diluted with chloroform/isopropanol mixture, washed with brine, dried, concentrated and column chromatographed to give the title compound (di-arylated) and 1-(4-nitro-phenylamino)-3-(2-nitro-4-trifluoromethanesulfonyl-phenoxy)-propan-2-ol (mono-arylated). 1H NMR (360 MHz, DMSO-d6) δ 8.63 (d, 1H), 8.37 (dd, 1H), 8.30 (d, J=8.8 Hz, 2H), 7.83 (d, 1H), 7.66 (d, J=8.8 Hz, 2H), 7.50 (dd, 1H), 7.42 (d, 1H), 7.31 (d, 1H), 4.91 (m, 1H), 4.76 (m, 2H), 4.15 (dd, 1H), 3.91 (dd, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 days
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated
  6. customcolumn chromatographed

Sources & evidence

ORD record
ord-80b9e375d35147db84b62c48090b6847
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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