Sodium Carbonate → 2-Phenyl-3-(4-tosyloxy-benzoyl)-indolizine

HRID 867173Notes

Reaction equation

HRID 867173 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[N:14]([CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:16]([O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17].C(=O)([O-])[O-].[Na+].[Na+]>ClC(Cl)C>[C:1]1([C:7]2[CH:8]=[C:9]3[N:14]([C:15]=2[C:31](=[O:32])[C:30]2[CH:29]=[CH:28][C:27]([O:26][S:16]([C:19]4[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=4)(=[O:18])=[O:17])=[CH:35][CH:34]=2)[CH:13]=[CH:12][CH:11]=[CH:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 961282-PhenylindolizineHCID 123901674-(Chlorocarbonyl)phenyl 4-methylbenzene-1-sulfonate

Product 1

HCID 128447982-Phenyl-3-(4-tosyloxy-benzoyl)-indolizineYield 52.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

In a flask, containing a solution of 6.5g (0.044 mol) of 2-phenylindolizine in 100 ml of dichlorethane, 12.4 g (0.04 mol) of 4-tosyloxy-benzoyl chloride were added at room-temperature. The mixture was stirred for 12 hours and then poured into a 10%-solution of sodium carbonate. The product which precipitated was washed to neutrality and recrystallized from carbon tetrachloride. In this manner, 2-phenyl-3-(4-tosyloxy-benzoyl)-indolizine was obtained in a yield of 52.3%. M.P. 177°-178° C.

Workup

  1. additionwere added at room-temperature
  2. customThe product which precipitated
  3. washwas washed to neutrality
  4. customrecrystallized from carbon tetrachloride

Sources & evidence

ORD record
ord-4b7bab82693540c99ededf9a5e360a7e
Source dataset
uspto-grants-1978_07
Patent number
US04103012

Reaction notes

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