Toluene → 5-[1-[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylmethylene]-3-(dimethylamino)-2-thioxo-4-thiazolidinone

HRID 467199

Reaction equation

HRID 467199 reaction equation
C1(C)C=CC=CC=1.[CH3:8][C:9]([C:12]1[CH:13]=[C:14]([C:23](=O)[CH3:24])[CH:15]=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:17]=1[OH:18])([CH3:11])[CH3:10].[CH3:26][N:27]([CH3:35])[N:28]1[C:32](=[O:33])[CH2:31][S:30][C:29]1=[S:34].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[CH3:11][C:9]([C:12]1[CH:13]=[C:14]([CH2:23][CH:24]=[C:31]2[S:30][C:29](=[S:34])[N:28]([N:27]([CH3:35])[CH3:26])[C:32]2=[O:33])[CH:15]=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:17]=1[OH:18])([CH3:8])[CH3:10]

Participants

6

Reactant 4

HCID 1140TolueneHCID 517165Ammonium AcetateHCID 6162963',5'-Bis(tert-butyl)-4'-hydroxyacetophenoneHCID 43419784(5H)-Thiazolone, 3-(dimethylamino)dihydro-2-thioxo-

Product 1

HCID 571138725-[1-[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylmethylene]-3-(dimethylamino)-2-thioxo-4-thiazolidinone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 675 ml of toluene were added 20.9 g of 1-[3,5-bis-(1,1-dimethylethyl)-4-hydroxyphenyl]ethanone, 13.3 g of N-dimethylaminorhodanine 6.5 g of ammonium acetate and about 20 ml of acetic acid. The mixture was heated at reflux temperature and any aqueous layer generated was collected in a Dean-Stark trap. Over the following 52 hours an additional 39 g of ammonium acetate and about 100 ml of acetic acid were added in increments and a total of 89.2 ml of aqueous phase was drawn off. Following workup by conventional techniques, 17.1 g of the desired subtitled intermediate was recovered.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature
  3. customany aqueous layer generated was collected in a Dean-Stark trap
  4. additionOver the following 52 hours an additional 39 g of ammonium acetate and about 100 ml of acetic acid were added in increments
  5. customwas recovered

Sources & evidence

ORD record
ord-84b2a061d95843958a953542e03d5df8
Source dataset
uspto-grants-1992_10
Patent number
US05158966

Linked notes

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