Hydrochloric Acid → HCID 11023322, compound

HRID 864654Notes

Reaction equation

[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH2:16][CH:17]2[S:21]C(=S)N[C:18]2=[O:23])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].[OH-:24].[Na+].Cl>C(OCC)(=O)C>[CH3:3][C:2]([C:5]1[CH:6]=[C:7]([CH2:16][CH:17]([SH:21])[C:18]([OH:23])=[O:24])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:1]

Participants

Conditions

Temperature: 15 °C

Procedure

To 114.5 g of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]-2-thioxo-4-thiazolidinone, 815 ml of 2M sodium hydroxide was added. The resultant mixture was heated to reflux temperature over the course of one hour and maintained at reflux for 2 hours. The mixture was cooled in an ice/water bath to 15° C. and 290 ml of 6M hydrochloric acid was added dropwise under a nitrogen atmosphere over 15 minutes, keeping the temperature of the mixture below 16° C. The resultant solid was dissolved by adding 600 ml of ethyl acetate to the mixture. The organic layer was separated, washed 3 times with 100 ml of saturated sodium chloride solution, dried over sodium sulfate and then the solvent was removed in vacuo to yield 100.3 g (100% of yield) of the subtitled intermediate. mp 137°-140° C.

Workup

temperatureto reflux temperature over the course of one hour
temperaturemaintained
temperatureat reflux for 2 hours
customthe temperature of the mixture below 16° C
dissolutionThe resultant solid was dissolved
customThe organic layer was separated
washwashed 3 times with 100 ml of saturated sodium chloride solution
dry with materialdried over sodium sulfate
customthe solvent was removed in vacuo
customto yield

Sources & evidence

ORD record: ord-e86e1e65b02347718c4d2404794f2972
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05563277

Reaction notes

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