Hydrochloric Acid → AL 321

HRID 1759337Notes

Reaction equation

HRID 1759337 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].Cl>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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 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
110 °C

Procedure

A mixture of 27 g of ethyl 2-chloro-3-[4-(2-methyl-2-phenylpropyloxy)phenyl]propionate, 11 g of thiourea and 60 ml of sulfolane is heated at 110° C. for 6 hours and, then, boiled with 10 ml of 2 N-sulfuric acid (or 2 ml of 6 N-HCl) for 16 hours. After cooling, 1 l of water is added and the oil is separated and allowed to stand for a while, whereupon crystals separate out. These crystals are recrystallized from benzene-ligroin. By the above procedure is obtained 19.9 g of 5-[4-(2-methyl-2-phenylpropyloxy)benzyl]thiazolidine-2,4-dione.

Workup

  1. temperatureAfter cooling
  2. customthe oil is separated
  3. customseparate out
  4. customThese crystals are recrystallized from benzene-ligroin

Sources & evidence

ORD record
ord-457b0376ae5a4526990503293513a4f1
Source dataset
uspto-grants-1982_07
Patent number
US04340605

Reaction notes

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