Water → HCID 19800237, compound

HRID 1646993Notes

Reaction equation

HRID 1646993 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:10]([CH:18]([CH3:20])[CH3:19])=[CH:11][N:12]3[C:17]=2[CH:16]=[CH:15][CH:14]=[CH:13]3)=[CH:4][CH:3]=1.[C:21](=[O:24])([O-:23])[O-].[K+].[K+].Cl[CH:28]([N:31]([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:32][CH2:33][CH2:34][CH3:35])[CH2:29][CH3:30].[OH2:40]>CS(C)=O>[C:2]([OH:1])(=[O:40])[C:21]([OH:23])=[O:24].[CH2:36]([N:31]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH2:30][O:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[C:10]([CH:18]([CH3:20])[CH3:19])=[CH:11][N:12]3[C:17]=2[CH:16]=[CH:15][CH:14]=[CH:13]3)=[CH:6][CH:7]=1)[CH2:37][CH2:38][CH3:39]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 19754321HCID 19754321, compoundHCID 19800241HCID 19800241, compound

Product 1

HCID 19800237HCID 19800237, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Into a solution of 0.01 mol of 1-[(4-hydroxyphenyl)thio]-2-isopropylindolizine in 80 ml of dimethylsulphoxide, there were added 5 g of anhydrous potassium carbonate and 0.015 mol of 1-chloro-di-n-butylamino-propane. The reaction medium was maintained under stirring for 24 hours and then poured into 500 ml of water. The solution was extracted with diethyl ether and the organic phase was washed with water, dried on sodium sulphate, filtered and evaporated to dryness to obtain the desired product in basic form. This crude compound was dissolved in dry diethyl ether and a solution of oxalic acid in diethyl ether was added.

Workup

  1. temperatureThe reaction medium was maintained
  2. extractionThe solution was extracted with diethyl ether
  3. washthe organic phase was washed with water
  4. customdried on sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-a37fad3531d8463a94bf802e16f99ab8
Source dataset
uspto-grants-1993_01
Patent number
US05182291

Reaction notes

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