HCID 13826056, compound → HCID 13826038, compound

HRID 1709290Notes

Reaction equation

HRID 1709290 reaction equation
[Cr](Cl)([O-])(=O)=[O:2].[NH+]1C=CC=CC=1.OCC[CH2:15][C:16]1[CH:34]=[CH:33][C:19]([CH2:20][CH2:21][NH:22][S:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])=[CH:18][CH:17]=1>C(Cl)Cl>[CH:15]([C:16]1[CH:34]=[CH:33][C:19]([CH2:20][CH2:21][NH:22][S:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])=[CH:18][CH:17]=1)=[O:2]

Participants

4

Reactant 2

HCID 13826056HCID 13826056, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 13826038HCID 13826038, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of 12.8 g. (59.4 mmole) pyridinium chlorochromate and 250 ml. methylene chloride are introduced, with stirring at ambient temperature, 14.0 g. (39.6 mmole) 4-chlorobenzenesulphonic acid-[4-(3-hydroxypropyl)-phenethylamide]. The reaction mixture is stirred for a further hour and then poured off from insolubles. The methylene chloride phase is chromatographed with a short column (silica gel/methylene chloride) and evaporated. Yield 10.8 g. (78% of theory); m.p. 65°-66° C. Oxime: m.p. 156°-158° C. (recrystallised from toluene).

Workup

  1. stirringThe reaction mixture is stirred for a further hour
  2. additionpoured off from insolubles
  3. customThe methylene chloride phase is chromatographed with a short column (silica gel/methylene chloride)
  4. customevaporated
  5. customOxime: m.p. 156°-158° C. (recrystallised from toluene)

Sources & evidence

ORD record
ord-27b883a860764f0daa58c7c738b3a816
Source dataset
uspto-grants-1990_08
Patent number
US04948809

Reaction notes

Loading…