Hydrochloric Acid → 5-[4-(6-Hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]-5-methylthiazolidine-2,4-dione

HRID 1030361Notes

Reaction equation

HRID 1030361 reaction equation
C([O:4][C:5]1[C:6]([CH3:35])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](Cl)([CH3:33])[C:28](OCC)=[O:29])=[CH:22][CH:21]=1)([CH3:17])[CH2:9][CH2:8]2)(=O)C.[NH2:36][C:37](N)=[S:38].S1(CCCC1)(=O)=[O:41].Cl>O.COCCO>[OH:4][C:5]1[C:6]([CH3:35])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][C:27]3([CH3:33])[S:38][C:37](=[O:41])[NH:36][C:28]3=[O:29])=[CH:24][CH:25]=1)([CH3:17])[CH2:9][CH2:8]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31347SulfolaneHCID 2723790ThioureaHCID 19822192Ethyl 3-[4-(6-acetoxy-2,5,7,8-tetramethylchroman-2-yl-methoxy)phenyl]-2-chloro-2-methylpropionate

Product 1

HCID 198222185-[4-(6-Hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]-5-methylthiazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent

Procedure

The procedure described in Example 3 was repeated, but using 1.17 g of ethyl 3-[4-(6-acetoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)phenyl]-2-chloro -2-methylpropionate (prepared as described in Preparation 46), 0.63 g of thiourea, 3 g of sulfolane, 10 ml of ethylene glycol monomethyl ether, 3 ml of water and 2 ml of 35% w/v aqueous hydrochloric acid, to give the title compound, softening at 69°-72° C.

Sources & evidence

ORD record
ord-ad184ec603eb460c8962ff3534d3c159
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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