Sulfolane → AL 321

HRID 326154Notes

Reaction equation

HRID 326154 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-19fa62cc574b4ae8a8087f1a2593285c
Source dataset
uspto-grants-1984_04
Patent number
US04444779

Reaction notes

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