Sodium Hydroxide → 5-[3,4-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1,3,4-thiadiazole-2(3H)-thione

HRID 466055Notes

Reaction equation

HRID 466055 reaction equation
CC([C:5]1[CH:6]=[C:7]([C:16]2[S:20][C:19](=[S:21])[NH:18][N:17]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])(C)C.[OH-].[Na+]>CO>[CH3:13][C:12]([CH:9]1[C:10]([C:7]([CH3:16])([CH3:8])[CH3:6])([OH:11])[CH:5]=[CH:6][C:7]([C:16]2[S:20][C:19](=[S:21])[NH:18][N:17]=2)=[CH:8]1)([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 30370185-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1,3,4-thiadiazole-2(3H)-thione

Product 1

HCID 867461955-[3,4-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1,3,4-thiadiazole-2(3H)-thioneYield 213.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 0° C. solution of 5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1,3,4-thiadiazole-2(3H)-thione (5.16 g, 0.0159 mole) in methanol (50 ml), is added aqueous 1.00M NaOH (15.9 ml, 0.0159 mole) dropwise. After the addition is complete the solution is stirred one hour at room temperature before concentrating in vacuo. The residue is slurried in toluene and concentrated. The product is transferred from the flask to a crystallizing dish and dried in vacuo at 80° C. for 48 hours to provide 5.5 g (5.5 g theor., 100%) of 5-[3,4-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1,3,4-thiadiazole-2(3H)-thione, monosodium salt.

Workup

  1. additionAfter the addition
  2. concentrationbefore concentrating in vacuo
  3. concentrationconcentrated
  4. customdried in vacuo at 80° C. for 48 hours

Sources & evidence

ORD record
ord-dcabdb5384cb47bbb6ab28fbd679ac0f
Source dataset
uspto-grants-1992_10
Patent number
US05155122

Reaction notes

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