Potassium Carbonate → HCID 18185347, compound

HRID 1358769Notes

Reaction equation

HRID 1358769 reaction equation
[OH:1][CH:2]([CH2:15][OH:16])[CH2:3][NH:4][C:5]1[CH:14]=[CH:13][C:8]([S:9]([NH2:12])(=[O:11])=[O:10])=[CH:7][CH:6]=1.Cl[C:18]1[CH:23]=[CH:22][C:21]([S:24]([C:27]([F:30])([F:29])[F:28])(=[O:26])=[O:25])=[CH:20][C:19]=1[N+:31]([O-:33])=[O:32].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(Cl)(Cl)Cl.C(O)(C)C>[OH:1][CH:2]([CH2:15][O:16][C:18]1[CH:23]=[CH:22][C:21]([S:24]([C:27]([F:29])([F:30])[F:28])(=[O:26])=[O:25])=[CH:20][C:19]=1[N+:31]([O-:33])=[O:32])[CH2:3][NH:4][C:5]1[CH:14]=[CH:13][C:8]([S:9]([NH2:12])(=[O:10])=[O:11])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 15479561-Chloro-2-nitro-4-trifluoromethanesulfonylbenzeneHCID 4430241HCID 4430241, compound

Product 1

HCID 18185347HCID 18185347, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

A mixture of N4-(2,3-dihydroxypropyl)sulfanilamide (82 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 (mono-arylated) and 4-[2,3-bis-(2-nitro-4-trifluoromethanesulfonyl-phenoxy)-propylamino]-benzenesulfonamide (di-arylated) example 62. 1H NMR (300 MHz, DMSO-d6) δ 8.63 (d, 1H), 8.35 (dd, 1H), 7.75 (d, 1H), 7.63 (d, 2H), 6.68 (d, 2H), 4.35 (d, 2H), 3.98 (t, 1H), 3.2 (m, 2H). MS −ve APCI 498 [M−1].

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-2280a269e4a44095980990243a2d1bfa
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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