Dimethylformamide → HCID 13938097, compound

HRID 865083Notes

Reaction equation

HRID 865083 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:12]=[CH:13][N:14]3[C:19]=2[CH:18]=[CH:17][CH:16]=[CH:15]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Br:20][CH2:21][CH2:22][CH2:23]Br.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Cl[CH2:37]Cl.C(O[C:42](=O)[CH3:43])C>>[Br:20][CH2:21][CH2:22][CH2:23][O:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]2[C:12]([CH:42]([CH3:43])[CH3:37])=[CH:13][N:14]3[C:19]=2[CH:18]=[CH:17][CH:16]=[CH:15]3)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 18931477HCID 18931477, compoundHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 13938097HCID 13938097, compound

Conditions

Temperature
100 °C

Procedure

3.15 g (0.01 mole) of 1-(4-hydroxybenzenesulfonyl) indolizine, 40.38 g (0.2 mole; 20.3 ml) of 1,3-dibromo propane, 1.66 g (0.012 mole) of potassium carbonate and 20 ml of N,N-dimethylformamide are mixed. The mixture is heated at 100° C. and the reaction is followed by thin layer chromatography (solvent: dichloromethane/ethylacetate 95/5). Reaction is allowed to proceed for 50 minutes, then the excess 1,3-dibromo propane is removed by evaporation under reduced pressure. The residue is taken up in ethyl acetate and washed with dilued sodium hydroxide, then with water. The organic phase is dried over potassium carbonate, then filtered. It is poured into water, extracted with ethylacetate, then washed with water and with a saturated solution of sodium chloride. It is dried over sodium sulfate and concentrated. In this manner, about 4 g of crude 1-[4-(3-bromopropoxy)benzenesulfonyl]2-isopropyl indolizine are obtained which are recrystallized from an ethyl acetate/hexane mixture.

Workup

  1. customReaction
  2. customthe excess 1,3-dibromo propane is removed by evaporation under reduced pressure
  3. washwashed with dilued sodium hydroxide
  4. dry with materialThe organic phase is dried over potassium carbonate
  5. filtrationfiltered
  6. additionIt is poured into water
  7. extractionextracted with ethylacetate
  8. washwashed with water and with a saturated solution of sodium chloride
  9. dry with materialIt is dried over sodium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-1f8aa413448b4456a5050f4ab954ebdb
Source dataset
uspto-grants-1996_10
Patent number
US05565470

Reaction notes

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