Hydrochloric Acid → AL 321

HRID 1903756Notes

Reaction equation

HRID 1903756 reaction equation
CS(O[CH:6]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]([CH3:29])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:22])=[CH:15][CH:14]=1)[C:7]([O:9]CC)=O)(=O)=O.[NH2:30][C:31](N)=[S:32].S1(CCCC1)(=O)=[O:35].Cl>O>[CH3:29][C:21]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([CH3:22])[CH2:20][O:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][CH:6]2[S:32][C:31](=[O:35])[NH:30][C:7]2=[O:9])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31347SulfolaneHCID 2723790ThioureaHCID 20462533HCID 20462533, compound

Product 1

HCID 194620AL 321

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

2.1 g Of ethyl 2-methanesulfonyloxy-3-[4-(2-methyl-2-phenylpropyloxy)phenyl]propionate and 0.76 g of thiourea are added to 20 ml of sulfolane, and the mixture is heated at 120° C. with stirring for one hour. After adding 10 ml of 2 N-hydrochloric acid, the mixture is heated at 100° C. for 8 hours. After cooling, water is added to the mixture, and the mixture is subjected to extraction with ether. The extract is washed with water and dried. The ether is distilled off to give 1.3 g of 5-[4-(2-methyl-2-phenylpropyloxy)benzyl]thiazolidine-2,4-dione.

Workup

  1. temperaturethe mixture is heated at 100° C. for 8 hours
  2. temperatureAfter cooling
  3. extractionthe mixture is subjected to extraction with ether
  4. washThe extract is washed with water
  5. customdried
  6. distillationThe ether is distilled off

Sources & evidence

ORD record
ord-a12067d06a4a4ac4ad416e347e1201aa
Source dataset
uspto-grants-1984_03
Patent number
US04438141

Reaction notes

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