Sulfolane → AL 321

HRID 1759336Notes

Reaction equation

HRID 1759336 reaction equation
Cl[CH:2]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]([CH3:25])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])=[CH:11][CH:10]=1)[C:3]([O:5]CC)=O.[NH2:26][C:27](N)=[S:28].S1(CCCC1)(=O)=[O:31]>O>[CH3:25][C:17]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([CH3:18])[CH2:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH:2]2[S:28][C:27](=[O:31])[NH:26][C:3]2=[O:5])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 31347SulfolaneHCID 194150Ethyl 2-chloro-3-[4-(2-methyl-2-phenylpropoxy)phenyl]propanoateHCID 2723790Thiourea

Product 1

HCID 194620AL 321

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3.6 g of ethyl 2-chloro-3-[4-(2-methyl-2-phenylpropyloxy)phenyl]propionate, 0.73 g of thiourea and 3 ml of sulfolane is heated at 120° C. for 4 hours and after cooling, 15 ml of water is added. The oil is separated, ether is added to the oil and the crystalline insolubles (a) are separated from the solution (b) by filtration. The filtrate (b) is distilled to remove the solvent and the residue is run onto a column of 100 g silica gel, elution being carried out with chloroform. By the above procedure is obtained 1.7 g of 5-[4-(2-methyl-2-phenylpropyloxy)benzyl]thiazolidine-2,4-dione. m.p. 107°-108° C. (benzene-ligroin)

Workup

  1. temperatureafter cooling
  2. customThe oil is separated
  3. additionether is added to the oil
  4. customthe crystalline insolubles (a) are separated from the solution (b) by filtration
  5. distillationThe filtrate (b) is distilled
  6. customto remove the solvent
  7. washthe residue is run onto a column of 100 g silica gel, elution

Sources & evidence

ORD record
ord-07826b023e5a465c96fca2ee7bcf24f4
Source dataset
uspto-grants-1982_07
Patent number
US04340605

Reaction notes

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